Development of Cross-Conjugated Vinylogous [4+2] Anionic Annulation. Application to the Total Synthesis of Natural Antibiotic ( ±)-ABX.

Development of Cross-Conjugated Vinylogous [4+2] Anionic Annulation. Application to the Total Synthesis of Natural Antibiotic (±)-ABX.
Angew Chem Int Ed Engl. 2020 Jan 16;:
Authors: Shia KS, Huang JK
Abstract
The cross-conjugated vinylogous [4+2] anionic annulation has been newly developed, the cascade process of which has a high preference for regiochemical control and chemoselectivity, giving rise to exclusively Michael-type adducts in moderate to high yields (up to 94%, 35 examples). By making use of this approach as a key operation, the first total synthesis of natural antibiotic ABX, in racemic form, has been successfully achieved in a concise 7-step sequence with an overall yield of ca. 20%.
PMID: 31944523 [PubMed - as supplied by publisher]

Source: Angewandte Chemie - January 15, 2020 Category: Chemistry Authors: Shia KS, Huang JK Tags: Angew Chem Int Ed Engl Source Type: research