3 years ago

Total Synthesis and Stereochemical Revision of Iriomoteolide-2a

Masashi Tsuda, Akihiro Hakamata, Haruhiko Fuwa, Keita Sakamoto
Total synthesis and stereochemical revision of iriomoteolide-2a, a cytotoxic marine macrolide natural product having an unusual 23-membered macrolactone skeleton, have been accomplished for the first time. The synthesis involves an asymmetric epoxidation/diepoxide cyclization cascade for the construction of the bis-tetrahydrofuran moiety, a Suzuki-Miyaura coupling for the fragment assembly, and a ring-closing metathesis for the closure of the macrocyclic backbone.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201800507

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