Total Synthesis and Determination of the Absolute Configuration of (−)-Dolabriferol

Angewandte Chemie International Edition 2010
Sylvain Laclef, Māris Turks, Pierre Vogel

A reaction cascade combining sulfur dioxide with a 1-oxy-1,3-diene and (E)-silyl enol ether formed the basis of a short total synthesis of (−)-dolabriferol. The absolute configuration of this natural product, which was first extracted from a gastropod mollusc in 1996, was established unequivocally.

Keywords
asymmetric synthesis;natural products;polypropionates;SO2 umpolung;stereotriads
DOI
10.1002/anie.201003735
Hyperlink
http://onlinelibrary.wiley.com/doi/10.1002/anie.201003735/abstract

Laclef, S., Turks, M., Vogel, P. Total Synthesis and Determination of the Absolute Configuration of (−)-Dolabriferol. Angewandte Chemie International Edition, 2010, Vol.49, Iss.45, pp.8525-8527. e-ISSN 1521-3773. Available from: doi:10.1002/anie.201003735

Publication language
English (en)