A Concise, Phosphate-Mediated Approach to the Total Synthesis of (−)-Tetrahydrolipstatin

View/ Open
Issue Date
2010-04Author
Venukadasula, Phanindra K. M.
Chegondi, Rambabu
Maitra, Soma
Hanson, Paul R.
Publisher
American Chemical Society
Type
Article
Article Version
Scholarly/refereed, author accepted manuscript
Rights
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/ol1002913
Metadata
Show full item recordAbstract
An efficient synthesis of (−)-tetrahydrolipstatin (THL) is reported. This method takes advantage of a phosphate tether-mediated, one-pot, sequential RCM/CM/hydrogenation protocol to deliver THL in 8 total steps from a readily prepared (S,S)-triene. The strategy incorporates selective cross metathesis, regio-selective hydrogenation, regio- and diastereoselective cuprate addition and Mitsunobu inversion for installation of the C5 formamide ester subunit.
Collections
Citation
Venukadasula, P. K. M., Chegondi, R., Maitra, S., & Hanson, P. R. (2010). A Concise, Phosphate-Mediated Approach to the Total Synthesis of (−)-Tetrahydrolipstatin. Organic Letters, 12(7), 1556–1559. http://doi.org/10.1021/ol1002913
Items in KU ScholarWorks are protected by copyright, with all rights reserved, unless otherwise indicated.
We want to hear from you! Please share your stories about how Open Access to this item benefits YOU.