First total synthesis of modiolide A, based on the whole-cell yeast-catalyzed asymmetric reduction of a propargyl ketone

While the first total synthesis of modiolide A ( 1a), a 10-membered ring lactone with a marine-origin was achieved, an important chiral building block for constructing the chirality at C-4 in 1a, ( S)-6-[(4-methoxybenzyl)oxy]-1-trimethylsilyl-1-hexyn-3-ol ( 3a) was obtained in as high as 96.1% ee. A...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron Vol. 63; no. 36; pp. 8752 - 8760
Main Authors Matsuda, Masaaki, Yamazaki, Takahiro, Fuhshuku, Ken-ichi, Sugai, Takeshi
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.09.2007
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Pichia
Science & Technology
METABOLITES
ENANTIOSELECTIVE SYNTHESIS
HIYAMA-KISHI REACTION
ENANTIOMERS
CONSTRUCTION
STEREOSELECTIVE-SYNTHESIS
INHIBITORS
KEY-STEP
EFFICIENT
CHOLESTEROL-BIOSYNTHESIS
Online AccessGet full text

Cover

More Information
Summary:While the first total synthesis of modiolide A ( 1a), a 10-membered ring lactone with a marine-origin was achieved, an important chiral building block for constructing the chirality at C-4 in 1a, ( S)-6-[(4-methoxybenzyl)oxy]-1-trimethylsilyl-1-hexyn-3-ol ( 3a) was obtained in as high as 96.1% ee. Asymmetric reduction of a silylated propargyl ketone ( 5) mediated by whole-cell of Pichia minuta IAM 12215 was established. This yeast-mediated reduction was also applicable to provide stereochemically pure (3 S,5 R)-5-[(4-methoxybenzyl)oxy]-1-trimethylsilyl-1-hexyn-3-ol ( 15), a synthetic intermediate for the related 10-membered lactone, tuckolide ( 16). [Display omitted]
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2007.06.038