Journal
TETRAHEDRON
Volume 68, Issue 24, Pages 4581-4587Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.04.035
Keywords
Rumphellaone; Cytotoxic; Total synthesis; Epoxy nitrile; Cyclobutane
Categories
Funding
- Ministry of Education, Culture, Sports, Science and Technology, Japan [22380064]
- Grants-in-Aid for Scientific Research [22380064] Funding Source: KAKEN
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The first enantioselective total synthesis of rumphellaone A, a cytotoxic 4,5-seco-caryophyllane isolated from the gorgonian coral Rumphella antipathies, has been achieved from a known olefinic alcohol by a 16-step sequence involving Stork's epoxy nitrile cyclization as the key step to concomitantly install a cyclobutane ring and three contiguous stereogenic centers contained in the molecule. (C) 2012 Elsevier Ltd. All rights reserved.
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