Journal
TETRAHEDRON LETTERS
Volume 55, Issue 8, Pages 1486-1487Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2014.01.050
Keywords
Terpendole; Indole diterpene; Antimitotic; Total synthesis; Epoxidation
Categories
Funding
- Ministry of Education, Culture, Sports, Science and Technology of Japan [22380064]
- Grants-in-Aid for Scientific Research [22380064] Funding Source: KAKEN
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Diastereoselective construction of a DEF ring model of terpendole E, a M phase-specific antimitotic natural product, has been achieved from a known bicyclic keto ester by a 10-step (or 12-step) sequence that features an efficient one-pot intramolecular etherification of an olefinic alcohol with mCPBA. The synthesis proceeded in an excellent overall yield of 36% through 10 steps or in 56% via 12 steps which involved a highly diastereoselective reduction of a ketone derived from an undesired diastereomeric alcohol intermediate. (C) 2014 Elsevier Ltd. All rights reserved.
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