Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 15, Issue 36, Pages 9223-9234Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200900776
Keywords
asymmetric synthesis; chiral auxiliaries; glycolate alkylation; ring-closing metathesis; total synthesis
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Funding
- National Institute for General Medical Sciences [GM60567]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM060567] Funding Source: NIH RePORTER
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Brevetoxin A is a decacyclic ladder toxin that possesses 5-, 6-, 7-, 8-, and 9-membered oxacycles, as well as 22 tetrahedral stereocenters. Herein, we describe a unified approach to the B, E, G, and J rings based upon a ring-closing metathesis strategy from the corresponding dienes. The enolate technologies developed in our-laboratory allowed access to the precursor acyclic dienes for the B, E, and G medium-ring ethers. The strategies developed for the syntheses of these four monocycles ultimately provided multigram quantities of each of the rings, supporting our efforts toward the completion of a convergent synthesis of brevetoxin A.
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