(−)-Lytophilippine A: Synthesis of a C1−C18 Building Block

The convergent enantioselective synthesis of a protected C1−C18 building block for the total synthesis of (−)-lytophilippine A was achieved. A catalytic asymmetric Gosteli−Claisen rearrangement and an Evans aldol reaction served as key C/C-connecting transformations during the assembling of the C1−C...

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Published inOrganic letters Vol. 12; no. 22; pp. 5258 - 5261
Main Authors Gille, Annika, Hiersemann, Martin
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.11.2010
Amer Chemical Soc
Subjects
Animals
Catalysis
Chemistry
Chemistry, Organic
Galactose - chemistry
Hydrozoa - chemistry
Macrolides - chemical synthesis
Macrolides - chemistry
Molecular Structure
Physical Sciences
Science & Technology
Stereoisomerism
ALLYL VINYL ETHER
ALCOHOLS
ACID
ENANTIOSELECTIVE CLAISEN REARRANGEMENT
NATURAL-PRODUCTS
EXACT-EXCHANGE
HYDROPEROXIDE
DENSITY-FUNCTIONAL THERMOCHEMISTRY
DERIVATIVES
CATALYSTS
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Summary:The convergent enantioselective synthesis of a protected C1−C18 building block for the total synthesis of (−)-lytophilippine A was achieved. A catalytic asymmetric Gosteli−Claisen rearrangement and an Evans aldol reaction served as key C/C-connecting transformations during the assembling of the C1−C7 subunit (10 steps from 4, 29%). The synthesis of the C8−C18 segment was achieved utilizing d-galactose as inexpensive ex-chiral-pool starting material (15 steps, 15%). The merger of the subunits was accomplished by a remarkably efficient sequence consisting of esterification and ring-closing metathesis (five steps, 56%).
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol1023008