A Convergent Synthesis of (+)‐Parviflorin, (+)‐Squamocin K, and (+)‐5 S ‐Hydroxyparviflorin | Zendy

Trost Barry M. | Zendy; Calkins Trevor L. | Zendy; Bochet Christian G. | Zendy

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A Convergent Synthesis of (+)‐Parviflorin, (+)‐Squamocin K, and (+)‐5 S ‐Hydroxyparviflorin

Author(s) -

Trost Barry M.,

Calkins Trevor L.,

Bochet Christian G.

Publication year - 1997

Publication title -

angewandte chemie international edition in english

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 0570-0833

DOI - 10.1002/anie.199726321

Subject(s) - acetogenin , alkyne , tetrahydrofuran , convergent synthesis , stereochemistry , chemistry , catalysis , organic chemistry , biology , botany , annonaceae , solvent

Thirty of the thirty‐five carbon atoms of the acetogenin (+)‐parviflorin ( 3 , also named squamocin E) in this highly convergent synthesis derive from one building block, the readily accessible alcohol 1 . The remaining five have their origin in an alkyne obtained from lactic acid. The key step of this general strategy to bis(tetrahydrofuran) acetogenins is a Ru‐catalyzed Alder–ene coupling of the alkyne with a bis(tetrahydrofuran) made from two units of 1 .

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