Concise Total Synthesis of (−)-Myxalamide A

The MIDA touch: A concise and highly convergent protecting‐group‐free total synthesis of (−)‐myxalamide A involves a stereoselective vinylogous Mukaiyama aldol reaction of a vinylketene silyl N,O‐acetal, together with a one‐pot Stille/Suzuki–Miyaura cross‐coupling reaction using Burke's N‐methy...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2012-07, Vol.51 (29), p.7271-7274
Main Authors: Fujita, Kazuhiro, Matsui, Ryosuke, Suzuki, Takahiro, Kobayashi, Susumu
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
aldol reaction
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
cross-coupling
Myxococcus xanthus - chemistry
polyene antibiotics
Polyenes - chemical synthesis
Polyenes - chemistry
protecting-group-free synthesis
Stereoisomerism
total synthesis
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Summary:The MIDA touch: A concise and highly convergent protecting‐group‐free total synthesis of (−)‐myxalamide A involves a stereoselective vinylogous Mukaiyama aldol reaction of a vinylketene silyl N,O‐acetal, together with a one‐pot Stille/Suzuki–Miyaura cross‐coupling reaction using Burke's N‐methyliminodiacetic acid (MIDA) boronate to connect left‐ and right‐hand fragments of the molecule (see scheme).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201203093