Concise, Asymmetric, Stereocontrolled Total Synthesis of Stephacidins A, B and Notoamide B
- 25 April 2007
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 129 (19) , 6336-6342
- https://doi.org/10.1021/ja070259i
Abstract
Concise asymmetric total syntheses of the fungal metabolites (−)-stephacidin A, (+)-stephacidin B, and (+)-notoamide B are described. Key features of these total syntheses include (1) a facile synthesis of (R)-allyl proline methyl ester, (2) a revised route toward the pyranoindole ring system, (3) a novel cross-metathesis strategy for the introduction of important functional groups, and (4) an SN2‘ cyclization to form the [2.2.2] bridged bicyclic ring system. Furthermore, our synthesis has taken advantage of microwave heating to shorten reaction times as well as increase yields for the preparation of vital intermediates.Keywords
This publication has 20 references indexed in Scilit:
- Notoamides A–D: Prenylated Indole Alkaloids Isolated from a Marine‐Derived Fungus, Aspergillus sp.Angewandte Chemie International Edition in English, 2007
- Chirospecific Synthesis of Spirocyclic β-Lactams and Their Characterization as Potent Type II β-Turn Inducing Peptide MimeticsThe Journal of Organic Chemistry, 2005
- Construction of Highly Functionalized Medium‐Sized Rings: Synthesis of Hyperforin and Perforatumone Model SystemsAngewandte Chemie International Edition in English, 2005
- Total Synthesis of Avrainvillamide (CJ-17,665) and Stephacidin BAngewandte Chemie International Edition in English, 2005
- Enantioselective Synthesis of Stephacidin BJournal of the American Chemical Society, 2005
- Direct Coupling of Pyrroles with Carbonyl Compounds: Short Enantioselective Synthesis of (S)‐KetorolacAngewandte Chemie International Edition in English, 2005
- Short, Enantioselective Total Synthesis of Stephacidin AAngewandte Chemie International Edition in English, 2005
- Stereocontrolled Total Synthesis of (+)-Paraherquamide BJournal of the American Chemical Society, 1996
- First EPR spectroscopic detection of photochemically generated carbonyloxyl radicals in solution under steady-state conditionsJournal of the American Chemical Society, 1988
- Structure of dineopentylbis(triethylphosphine)platinum(II) and bis(triethylphosphine)-3,3-dimethylplatinacyclobutane. Reactant and product in a thermal cyclometalation reactionOrganometallics, 1982