Synthesis of Saturated Oxygenated Heterocycles I: 5- and 6-Membered Rings

288 Pages·2014·19.987 MB·English

by  Janine Cossy (eds.)

Topics in Heterocyclic Chemistry 35
Series Editor: B.U.W. Maes
Janine Cossy Editor
Synthesis of
Saturated
Oxygenated
Heterocycles I
5- and 6-Membered Rings
35
Topics in Heterocyclic Chemistry
Series Editors
B.U.W. Maes, Antwerpen, Belgium
Janine Cossy, Paris, France
Slovenko Polanc, Ljubljana, Slovenia
Editorial Board:
D. Enders, Aachen, Germany
S.V. Ley, Cambridge, UK
G. Mehta, Bangalore, India
K.C. Nicolaou, La Jolla, CA, USA
R. Noyori, Hirosawa, Japan
L.E. Overmann, Irvine, CA, USA
A. Padwa, Atlanta, GA, USA
For furthervolumes:
http://www.springer.com/series/7081
Aims and Scope
The series Topics in Heterocyclic Chemistry presents critical reviews on present
andfuturetrendsintheresearchofheterocycliccompounds.Overallthescopeisto
covertopicsdealingwithallareaswithinheterocyclicchemistry,bothexperimental
andtheoretical,ofinteresttothegeneralheterocyclicchemistrycommunity.
The series consists of topic related volumes edited by renowned editors with
contributionsofexpertsinthefield.
Janine Cossy
Editor
Synthesis of Saturated
Oxygenated Heterocycles I
5- and 6-Membered Rings
With contributions by
M.A. Brimble (cid:129) K.P. Kaliappan (cid:129) A.J. Moreno-Vargas (cid:129)
K.Palanichamy(cid:129)M.A.Perry(cid:129)J.D.Rainier(cid:129)S.D.Rychnovsky(cid:129)
N. Sizemore (cid:129) L.A. Stubbing (cid:129) P. Vogel
Editor
JanineCossy
ESPCI
LaboratoryofOrganicChemistry
ParisCedex05
France
ISSN1861-9282 ISSN1861-9290(electronic)
ISBN978-3-642-41472-5 ISBN978-3-642-41473-2(eBook)
DOI10.1007/978-3-642-41473-2
SpringerHeidelbergNewYorkDordrechtLondon
LibraryofCongressControlNumber:2014931980
©Springer-VerlagBerlinHeidelberg2014
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Preface
Two volumes are dedicated to the synthesis of saturated oxygenated heterocycles
and consist of eight chapters covering the synthesis of 5- to 16-membered ring
cyclic ethers and lactones. Rather than offer an exhaustive description of the
synthesisofcyclicethersandlactones,these volumespresentmethodsandstrate-
giestosynthesizeheterocyclesandthushelpingthereadertofindsuitablemethods
for obtaining a desired saturated oxygenated heterocycle. The first volume com-
prisesfivechaptersandthesecondvolumethreechapters.
In chapter entitled “Synthesis of Substituted Tetrahydrofurans,” J. D. Rainier
outlinestheadvancesthathavebeenmadeduringthelast10yearsinthesynthesis
of tetrahydrofurans such as nucleophilic additions to acetals and hemiacetals,
cycloadditions, oxidative cyclizations, furan reductions, Prins-pinacol cascades,
ring-openingofbicyclicsubstrates,andnucleophilicsubstitutions.
Inchapter“SynthesisofSaturatedTetrahydropyrans,”S.D.Rychnovsky,M.A.
Perry, and N. Sizemore review the common strategies to access tetrahydropyrans
suchastheformationofO1–C2,C2–C3,C3–C4,O1–C6,andC2–C3bonds,aswell
asC2functionalizationoflactolsandlactones.
The chapter “Synthesis of Saturated Six-Membered Ring Lactones” by K. P.
Kaliappan and K. Palanichamy describes various selected methods such as
lactonization of δ-hydroxy acid derivatives, oxidation, electrophilic cyclization,
intramolecular nucleophilic displacement, radical and reductive cyclizations, pal-
ladium-catalyzedlactonization,aswellascarbonylationandcarboxylation.
Thesynthesisof7-oxabicyclo[2.2.1]heptanes andderivativesis reported inthe
chapter“Synthesisof7-Oxabicyclo[2.2.1]heptaneandDerivatives”hasbeenwrit-
tenbyP.VogelandA.J.Moreno-Vargas.Mostofthemethods,reportedtoaccess
7-oxabicyclo[2.2.1]heptanes,areDiels–Alderreactions,butnon-Diels–Alderreac-
tionssuchaselectrophiliccyclizationshavealsobeenincludedinthischapter.As
7-oxabicyclo[2.2.1]heptanederivativescanbegoodprecursorsofotheroxygenated
heterocycles, their ring cleavage either by cleavage of a C-O or a C-C bond have
beenreported.Inaddition,as7-oxabicyclo[2.2.1]heptanederivativesareextremely
v
vi Preface
usefulsynthons,fewsynthesesofnaturalproductsandbioactivecompounds,using
thesesynthons,havebeendescribed.
In chapter “Synthesis of 5,6-and 6,6-Spirocyclic Compounds,” M. A.Brimble
and L. A. Stubbing describe a number of recently reported and useful methods to
synthesize5,6-and6,6-spirocycliccompounds, including their applications tothe
synthesisofnaturalproductsandbioactivecompoundscontainingspiroacetalscaf-
folds. One can find dehydrative spirocyclization ofdihydroxyketones, metal-cata-
lyzed addition/elimination of allylic alcohols, acid-catalyzed spirocyclization of
hemiacetals,spirocyclizationofexo-andendocyclicenolethers,transition-metal-
catalyzedhydroalkoxylationofalkynes,electrophiliccyclizationandoxa-Michael
cyclization,intramolecularhetero-Michaeladdition,ring-openingofepoxidesand
cyclopropanes, cycloadditions, furan oxidation, intramolecular hydrogen abstrac-
tion,reductivecyclizations,ring-closingmetathesis,andrearrangements.
Inchapter“SynthesisofSeven-Membered-RingEthersandLactones,”O.Piva
describes the access to saturated oxygenated 7-membered cyclic ethers, by ring
expansion of oxygenated structures, by formation of C–O and C–C bonds using
differentmethods.For7-memberedcycliclactones,oxidativeprocesses,halolacto-
nization, lactonization of ω-hydroxyacids, tandem Suzuki coupling and
lactonization,andringenlargementarereported.
For the synthesis of 8- to 10-membered ring ethers, in chapter “Synthesis of
Eight-toTen-Membered-RingEthers,”J.M.ContellesandE.Sorianofocusonthe
formationofcarbon–carbondoublebondsbymetathesis,aswellasontheforma-
tion of carbon–carbon single bonds. The authors also report on the cyclization to
formC–Obonds,ringexpansion,ring-opening,andrearrangement.
Chapter “Synthesis of 12- to 16-Membered-Ring Lactones” is dedicated to the
synthesis of 12- to 16-membered ring lactones. In this chapter, M. Kalesse and
M.Cordespresentanoverviewofthemacrocyclizationofseco-acidsaswellasnew
effective procedures to access 12- to 16-membered ring lactones such as ring-
closingmetathesesofalkynesandolefins.Theauthorsalsoreporttheuseofketene
sourcesandbenzodioxinonestoproducemacrocycliclactones.Nitrileoxide-olefin
cycloaddition, intramolecular C–H oxidative macrolactonization, and Yamaguchi
and Mukaiyama macrocyclization as well as macrolactonization via thioester or
usingphosphorusreagentsaredescribed.
Iwouldliketoexpressmysinceregratitudetoalltheauthorsofthesechapters
for their effortsand outstandingcontributions.Iwould also liketothank B.Maes
forgivingmetheopportunitytoeditthesetwovolumes,toElizabethHawkinsand
TanjaJaegerfromSpringerforcoordinatingtheproject,andtoFairinMiriamJohn
Bennetfortheeditingprocess,forherhelpandpatience.
Finally, I hope that this book will be a good source of inspiration for those
planning the synthesis of saturated oxygenated heterocycles, for solving specific
syntheticproblems,orforelaboratingonnewsynthetictools.
Paris,France JanineCossy
Contents for Volume I
SynthesisofSubstitutedTetrahydrofurans. . . . . . . . . . . . . . . . . . . . . . 1
JonD.Rainier
SynthesisofSaturatedTetrahydropyrans. . . . . . . . . . . . . . . . . . . . . . . 43
MatthewA.Perry,ScottD.Rychnovsky,andNicholasSizemore
SynthesisofSaturatedSix-MemberedRingLactones. . . . . . . . . . . . . . 97
KalanidhiPalanichamyandKrishnaP.Kaliappan
Synthesisof7-Oxabicyclo[2.2.1]heptaneandDerivatives. . . . . . . . . . . . 141
AntonioJ.Moreno-VargasandPierreVogel
Synthesisof5,6-and6,6-SpirocyclicCompounds. . . . . . . . . . . . . . . . . . 189
MargaretA.BrimbleandLouiseA.Stubbing
Index. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 269
vii
ThiSisaFMBlankPage
Contents for Volume II
SynthesisofSeven-MemberedRingEthersandLactones. . . . . . . . . . . 283
OlivierPiva
SynthesisofEight-toTen-MemberedRingEthers. . . . . . . . . . . . . . . . 321
ElenaSorianoandJose´ Marco-Contelles
Synthesisof12-to16-Membered-RingLactones. . . . . . . . . . . . . . . . . . 369
MartinCordesandMarkusKalesse
Index. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 429
ix