An Approach Toward the Bridged 14‐Membered Carbon Macrocycle of Bielschowskysin | Zendy

Farcet JeanBaptiste | Zendy; Mulzer Johann | Zendy; Himmelbauer Martin K. | Zendy

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An Approach Toward the Bridged 14‐Membered Carbon Macrocycle of Bielschowskysin

Author(s) -

Farcet JeanBaptiste,

Mulzer Johann,

Himmelbauer Martin K.

Publication year - 2016

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201600271

Subject(s) - chemistry , tetradecane , intramolecular force , diterpene , carbonylation , alkylation , lactone , halide , palladium , sequence (biology) , stereochemistry , catalysis , organic chemistry , biochemistry , carbon monoxide

Relying on our previous achievements toward the a total synthesis of bielschowskysin,[1][J.‐B. Farcet, 2012], [2][J.‐B. Farcet, 2013], [3][M. Himmelbauer, 2013], [4][M. Himmelbauer, 2013], [5][J.‐B. Farcet, 2013] we herein report additional efforts to close the bridged tetradecane carbocyclic core of this marine diterpene. The key step of this strategy is an intramolecular alkylation between a cis ‐substituted vinyl halide and a lactone that were accessed by a diastereoselective propargylation/hydrogenation sequence and palladium‐catalyzed carbonylation, respectively.

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