Synthesis of a chiral steroid ring D precursor starting from carvone

A chiral five-membered, silyl enol ether containing, steroid ring D precursor has been synthesized from carvone. This silyl enol ether has been applied in the synthesis of a chiral C17 functionalized steroid skeleton using the addition of a carbocation, generated with ZnBr 2 from a Torgov reagent, f...

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Bibliographic Details
Published inTetrahedron Vol. 62; no. 8; pp. 1743 - 1748
Main Authors Pogrebnoi, Serghei, Sarabèr, Florence C.E., Jansen, Ben J.M., de Groot, Aede
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 20.02.2006
Elsevier
Subjects
(r)-2,3-o-isopropylideneglyceraldehyde
(s)-2,3-o-isopropylideneglyceraldehyde
building-block
C,D-trans steroid synthesis
Carvone
cd ring
Chemistry
Chemistry, Organic
Chiral silyl enol ethers
enantioselective synthesis
induction
Mukaiyama–Michael addition
Physical Sciences
rearrangement
reductive cleavage
route
Science & Technology
vitamin-d3
Chiral silyl enol ethers
Carvone
Mukaiyama–Michael addition
C,D-trans steroid synthesis
ROUTE
ENANTIOSELECTIVE SYNTHESIS
Mukaiyama-Michael addition
carvone
INDUCTION
REARRANGEMENT
REDUCTIVE CLEAVAGE
(R)-2,3-O-ISOPROPYLIDENEGLYCERALDEHYDE
chiral silyl enol ethers
CD RING
BUILDING-BLOCK
(S)-2,3-O-ISOPROPYLIDENEGLYCERALDEHYDE
VITAMIN-D3
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Summary:A chiral five-membered, silyl enol ether containing, steroid ring D precursor has been synthesized from carvone. This silyl enol ether has been applied in the synthesis of a chiral C17 functionalized steroid skeleton using the addition of a carbocation, generated with ZnBr 2 from a Torgov reagent, followed by cyclization of the adduct by treatment with acid. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2005.11.057