Acid-catalysed Skeletal Rearrangement of an Epoxy Derivative of Terrecyclic Acid A. Formation of a 5-Oxatetracyclo4,13.010,13>tridecane Derivative

DOI: 10.1039/c39910001598

Source and publish data:

Journal of the Chemical Society. Chemical communications p. 1598 - 1599 (1991)

Update date:2022-07-29

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Authors:

Hirota, Hiroshi

Kakita, Shingo

Hirota, Akira

Nakagawa, Masahira

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Article abstract of DOI:10.1039/c39910001598

Treatment of the epoxide 3 which is derived from a sesquiterpene antitumor antibiotic, terrecyclic acid A 1, with BF3*OEt2 in benzene, affords a skeletally rearranged ether 6 as the sole product; its structure was deduced from spectroscopic data including, 2D NMR data, to be <1S,2S,4R,7R,10S,13R>-2-hydroxy-11,11-dimethyl-5-oxatetracyclo<5.5.1.0^4,13.0^10,13>tridecan-1-ylmethanol.

Full text of DOI:10.1039/c39910001598

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