Reiterative Synthesis of trans‐Fused Polytetrahydropyrans Using the Oxiranyl Anion
- 1 June 1997
- journal article
- concept
- Published by Wiley in Chemistry – A European Journal
- Vol. 3 (6) , 849-852
- https://doi.org/10.1002/chem.19970030604
Abstract
The oxiranyl anion is a very unstable nucleophilic epoxide. This previously uncommon nucleophile has now been used for the synthesis of polycyclic ethers. Alkylation of an oxiranyl anion, a three‐carbon building block, with a triflate derived from tetrahydropyran‐methanol followed by acid‐catalyzed 6‐endo cyclization provides a trans‐fused bicyclic compound. Reiterative application of this procedure enables the rapid construction of trans‐fused polytetrahydropyrans.Keywords
This publication has 47 references indexed in Scilit:
- A New Strategy for the Reiterative Synthesis of trans-Fused Tetrahydropyrans via Alkylation of Oxiranyl Anion and 6-endo CyclizationJournal of the American Chemical Society, 1996
- An Iterative Approach to Biologically Important Fused Polycyclic Ethers via Acyl Radical CyclizationsThe Journal of Organic Chemistry, 1996
- The First Example of Oxiranyllithium and Oxiranyl Grignard Reagent Having a Carbanion Destabilizing Group: Generation, Property, and Some Synthetic UsesTetrahedron Letters, 1995
- Total Synthesis of Hemibrevetoxin BTetrahedron Letters, 1995
- Efficient Synthesis of the Ring System in Hemibrevetoxin-B via Lactone Enol Triflate MethodSynlett, 1995
- Stereocontrolled synthesis of the hemibrevetoxin ring system via an allylic tin methodJournal of the Chemical Society, Chemical Communications, 1993
- Synthesis of the C- and D-Ring System of Hemibrevetoxin-BChemistry Letters, 1992
- A new approach to the construction of .beta.-alkoxy-substituted cyclic ethers via the intramolecular cyclization of .omega.-trialkylplumbyl and .omega.-trialkylstannyl ether acetalsThe Journal of Organic Chemistry, 1990
- Phenylsulphonyl oxirane: a versatile reagent for organic synthesisJournal of the Chemical Society, Chemical Communications, 1988
- Methods for pyranoannulation: an approach to a new class of polyethersThe Journal of Organic Chemistry, 1985