The Daphniphyllum Alkaloids: Total Synthesis of (−)-Calyciphylline N | Zendy

Artem Shvartsbart | Zendy; Amos B. Smith | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Open Access

The Daphniphyllum Alkaloids: Total Synthesis of (−)-Calyciphylline N

Author(s) -

Artem Shvartsbart,

Amos B. Smith

Publication year - 2015

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja503899t

Subject(s) - chemistry , total synthesis , stereochemistry

Presented here is a full account on the development of a strategy culminating in the first total synthesis of the architecturally complex daphniphyllum alkaloid, (-)-calyciphylline N. Highlights of the approach include a highly diastereoselective, intramolecular Diels-Alder reaction of a silicon-tethered acrylate; an efficient Stille carbonylation of a sterically encumbered vinyl triflate; a one-pot Nazarov cyclization/proto-desilylation sequence; and the chemoselective hydrogenation of a fully substituted diene ester.

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research