Total Synthesis of (+)-18-epi-Latrunculol A: Development of a Synthetic Route | Zendy

Brett Williams | Zendy; Amos B. Smith | Zendy

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Total Synthesis of (+)-18-epi-Latrunculol A: Development of a Synthetic Route

Author(s) -

Brett Williams,

Amos B. Smith

Publication year - 2014

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/jo501733m

Subject(s) - chemistry , enone , total synthesis , enantioselective synthesis , alkynylation , stereochemistry , metathesis , congener , organic chemistry , catalysis , polymer , polymerization

The evolution of an enantioselective total synthesis of (+)-18-epi-latrunculol A, a congener of the marine-sponge-derived latrunculins A and B, is reported. Key steps include a late-stage Mitsunobu macrolactonization to construct the 16-membered macrolactone, a mild Carreira alkynylation to unite the northern and southern hemispheres, a diastereoselective, acid-mediated δ-hydroxy enone cyclization/equilibration sequence, and a functional-group-tolerant cross-metathesis to access the enone cyclization precursor.

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