Synthesis and Absolute Stereochemistry of Roseophilin
- 10 August 2001
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 123 (35) , 8509-8514
- https://doi.org/10.1021/ja011242h
Abstract
The enantiospecific total synthesis of natural roseophilin has been completed in 7.0% overall yield over 15 steps by means of an asymmetric cyclopentannelation. This establishes the absolute configuration of the natural product as 22R,23R. Cyclopentenone (+)-12 was prepared in 78% yield and 86% ee in the key step.Keywords
This publication has 11 references indexed in Scilit:
- Asymmetric Cyclopentannelation. Chiral Auxiliary on the AlleneOrganic Letters, 2000
- A new approach to the core of roseophilinTetrahedron Letters, 1999
- A Formal Total Synthesis of Roseophilin: Cyclopentannelation Approach to the Macrocyclic CoreOrganic Letters, 1999
- Studies toward the total synthesis of antibiotic roseophilin: A novel synthesis of the macrotricyclic partTetrahedron Letters, 1998
- Michael Additions to (R)-1-Acetyl-5-isopropoxy-3-pyrrolin-2-one and Subsequent N-Acyliminium Ion Generation: Synthesis of Enantiopure 1-Azabicycles and Preparation of an Intermediate for a Projected Synthesis of RoseophilinThe Journal of Organic Chemistry, 1998
- Structure of a new antibiotic, roseophilinTetrahedron Letters, 1992
- A Convenient Method for the Preparation of N-MethoxyamidesSynthetic Communications, 1990
- The vinylogation of aldehydes: An improved method for the preparation of alpha formylethylidenetriphenylphosphorane, and an improved alpha silyl imine reagent of propionaldehydeTetrahedron Letters, 1985
- Total synthesis of racemic sesbanineThe Journal of Organic Chemistry, 1980
- Stereoselective energy transfer induced by circularly polarized lightJournal of the American Chemical Society, 1979