Development of a Cross‐Conjugated Vinylogous [4+2] Anionic Annulation and Application to the Total Synthesis of Natural Antibiotic (±)‐ABX | Zendy

Huang JingKai | Zendy; Shia KakShan | Zendy

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

Author(s) -

Huang JingKai,

Shia KakShan

Publication year - 2020

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201914657

Subject(s) - chemoselectivity , annulation , abx test , total synthesis , conjugated system , chemistry , adduct , yield (engineering) , organic chemistry , stereochemistry , combinatorial chemistry , catalysis , mathematics , materials science , statistics , polymer , metallurgy

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 about 20 %.

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