Total Synthesis of Amphidinolide E
- 30 November 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (50), 15960-15961
- https://doi.org/10.1021/ja066663j
Abstract
A convergent and highly stereocontrolled synthesis of amphidinolide E (1) has been accomplished. The synthesis features a highly diastereoselective (>20:1) BF3·Et2O promoted [3+2] annulation reaction between aldehyde 3 and allylsilane 4 to afford substituted tetrahydrofuran 2.Keywords
This publication has 40 references indexed in Scilit:
- Total Synthesis of Bengamide E and Analogues by Modification at C-2 and at Terminal Olefinic PositionsThe Journal of Organic Chemistry, 2005
- [3 + 2]-Annulation Reactions of Chiral Allylsilanes and Chiral Aldehydes. Studies on the Synthesis of Bis-tetrahydrofuran Substructures of Annonaceous AcetogeninsThe Journal of Organic Chemistry, 2005
- [3 + 2] Annulation of Allylic Silanes in Acyclic Stereocontrol: Total Synthesis of (9S)-Dihydroerythronolide AJournal of the American Chemical Society, 2003
- Cuprous Chloride Accelerated Stille Reactions. A General and Effective Coupling System for Sterically Congested Substrates and for Enantioselective SynthesisJournal of the American Chemical Society, 1999
- Double stereodifferentiation in the Lewis acid-promoted addition of chiral (E)-crotylsilanes with (S)-2-(benzyloxy)propanal. Effect of Lewis acid on reaction diastereoselectionThe Journal of Organic Chemistry, 1993
- Asymmetric synthesis using tartrate ester modified allylboronates. 2. Single and double asymmetric reactions with alkoxy-substituted aldehydesThe Journal of Organic Chemistry, 1990
- Asymmetric synthesis using tartrate ester modified allylboronates. 1. Factors influencing stereoselectivityThe Journal of Organic Chemistry, 1990
- Amphidinolide E, a novel antileukemic 19-membered macrolide from the cultured symbiotic dinoflagellate Amphidinium spThe Journal of Organic Chemistry, 1990
- Scope and mechanism of stannylalumination of 1-alkynesThe Journal of Organic Chemistry, 1989
- Sulfur trioxide in the oxidation of alcohols by dimethyl sulfoxideJournal of the American Chemical Society, 1967