ENANTIOSELECTIVE TOTAL SYNTHESIS OF (-)-SCABRONINE D

The first enantioselective total synthesis of (-)-scabronine D comprising a unique bridged hemiacetal is described. The total synthesis is successfully accomplished using an enantiopure intermediate prepared in the total synthesis of (-)-scabronines G and A, and (-)-episcabronine A. Because the adva...

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Bibliographic Details
Published inHeterocycles Vol. 89; no. 3; pp. 669 - 677
Main Authors Kobayakawa, Yu, Nakada, Masahisa
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 2014
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SYSTEM
CYATHANE DITERPENES
MUSHROOM
ESTERS
CYATHINS
(+/-)-ALLOCYATHIN B-2
SCABRONINE
SECRETION
NERVE GROWTH-FACTOR
SKELETON
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Summary:The first enantioselective total synthesis of (-)-scabronine D comprising a unique bridged hemiacetal is described. The total synthesis is successfully accomplished using an enantiopure intermediate prepared in the total synthesis of (-)-scabronines G and A, and (-)-episcabronine A. Because the advanced intermediate was found to be sensitive to basic reaction conditions, the C14 keto and C11 hydroxy groups had to be co-protected as methyl acetal. In addition, both the C15 hydroxy and C17 carboxyl groups were too reactive to be chemically discriminated; hence, the carboxyl group once formed was protected as a tert-butyl ester for ensuring successful transformations.
Bibliography:KAKEN
ISSN:0385-5414
1881-0942
DOI:10.3987/COM-13-12921