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Convergent Total Syntheses of (−)‐Rubriflordilactone B and (−)‐ pseudo ‐Rubriflordilactone B
Author(s) -
Mohammad Mujahid,
Chintalapudi Venkaiah,
Carney Jeffrey M.,
Mansfield Steven J.,
Sanderson Pollyanna,
Christensen Kirsten E.,
Anderson Edward A.
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201908917
Subject(s) - natural product , total synthesis , rhodium , aldehyde , alkyne , chemistry , ring (chemistry) , stereochemistry , convergent synthesis , catalysis , organic chemistry
A highly convergent strategy for the synthesis of the natural product (−)‐rubriflordilactone B, and the proposed structure of (−)‐ pseudo ‐rubriflordilactone B, is described. Late stage coupling of diynes containing the respective natural product FG rings with a common AB ring aldehyde precedes rhodium‐catalyzed [2+2+2] alkyne cyclotrimerization to form the natural product skeleton, with the syntheses completed in just one further operation. This work resolves the uncertainty surrounding the identity of pseudo ‐rubriflordilactone B and provides a robust platform for further synthetic and biological investigations.