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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 .