Enantioselective Synthesis of the C1–C6 and C7–C23 Fragments of the Proposed Structure of Iriomoteolide 1a

Synthesis of the C1–C6 and C7–C23 fragments of the proposed structure of iriomoteolide 1a has been accomplished. Key steps include a cross metathesis to form the C15–C16 E olefin and a chelation controlled Grignard addition to form the tertiary alcohol at C14. Notably, 7 of the 9 stereocenters of th...

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Bibliographic Details
Published in:Organic letters 2012-05, Vol.14 (9), p.2366-2369
Main Authors: Crimmins, Michael T, Dechert, Anne-Marie R
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Macrolides - chemical synthesis
Macrolides - chemistry
Molecular Structure
Stereoisomerism
Thiazolidines - chemistry
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Summary:Synthesis of the C1–C6 and C7–C23 fragments of the proposed structure of iriomoteolide 1a has been accomplished. Key steps include a cross metathesis to form the C15–C16 E olefin and a chelation controlled Grignard addition to form the tertiary alcohol at C14. Notably, 7 of the 9 stereocenters of the proposed structure have been set using various aldol reactions employing metallo enolates of thiazolidinethiones.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol300785c