Total Synthesis of (-)-Phorbaketal A

A convergent asymmetric total synthesis of phorbaketal,A was achieved in 10 steps through a Au(I)-catalyzed intramolecular spiroketalization reaction of an alkyne, diol intermediate prepared from (R)-catvone and geranial. The spirciketalization reaction was ratio, and stereoselective and was accompanied by isomerization of an exo-olefin into the trisubstittned olefin to form a unique spiroketal structure of phorbaketals.
Publisher
AMER CHEMICAL SOC
Issue Date
2017-07
Language
English
Keywords

SPONGE PHORBAS SP; AUSTRALIAN MARINE SPONGE; ALLYLIC ALCOHOLS; NATURAL-PRODUCTS; STEREOSELECTIVE-SYNTHESIS; PROMOTED REARRANGEMENT; STRUCTURE ELUCIDATION; EFFICIENT ACCESS; EPOXIDES; SPIRASTRELLOLIDE

Citation

ORGANIC LETTERS, v.19, no.14, pp.3903 - 3906

ISSN
1523-7060
DOI
10.1021/acs.orglett.7b01797
URI
http://hdl.handle.net/10203/225480
Appears in Collection
CH-Journal Papers(저널논문)
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