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A new approach to the pseudopterosins using an arene alkylation with a gamma-methylene-gamma-butyrolactone

A new approach to the pseudopterosins using an arene alkylation with a gamma-methylene-gamma-butyrolactone
A new approach to the pseudopterosins using an arene alkylation with a gamma-methylene-gamma-butyrolactone
A short and practical route to the tricyclic core of an unnatural pseudopterosin diastereoisomer is presented. Key features are an arene alkylation with a gamma -methylene-gamma -butyrolactone, viz. 10 --> 14, and an elaborate reduction sequence 14 --> 17 which both proceed diastereoselectively.
annulation, cyclisation, lactones, natural products, terpenes and terpenoidsenantioselective synthesis, stereochemistry, route, functionality, intermediate, elisabethae, chemistry, aglycone
0040-4039
1193-1195
Harrowven, D. C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Wilden, J. D.
c856b6d1-87fa-47f9-bbb7-08eeae14d5b5
Tyte, M. J.
4f091524-6ed0-49f5-baa4-34ea8b7bcf82
Hursthouse, M. B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Coles, S. J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Harrowven, D. C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Wilden, J. D.
c856b6d1-87fa-47f9-bbb7-08eeae14d5b5
Tyte, M. J.
4f091524-6ed0-49f5-baa4-34ea8b7bcf82
Hursthouse, M. B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Coles, S. J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8

Harrowven, D. C., Wilden, J. D., Tyte, M. J., Hursthouse, M. B. and Coles, S. J. (2001) A new approach to the pseudopterosins using an arene alkylation with a gamma-methylene-gamma-butyrolactone. Tetrahedron Letters, 42 (6), 1193-1195. (doi:10.1016/S0040-4039(00)02207-3).

Record type: Article

Abstract

A short and practical route to the tricyclic core of an unnatural pseudopterosin diastereoisomer is presented. Key features are an arene alkylation with a gamma -methylene-gamma -butyrolactone, viz. 10 --> 14, and an elaborate reduction sequence 14 --> 17 which both proceed diastereoselectively.

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More information

Published date: 5 February 2001
Keywords: annulation, cyclisation, lactones, natural products, terpenes and terpenoidsenantioselective synthesis, stereochemistry, route, functionality, intermediate, elisabethae, chemistry, aglycone

Identifiers

Local EPrints ID: 19511
URI: http://eprints.soton.ac.uk/id/eprint/19511
ISSN: 0040-4039
PURE UUID: a4c0b83d-4ae4-4221-baa1-aa691aadbdb4
ORCID for D. C. Harrowven: ORCID iD orcid.org/0000-0001-6730-3573
ORCID for S. J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

Catalogue record

Date deposited: 14 Feb 2006
Last modified: 16 Mar 2024 03:05

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Contributors

Author: D. C. Harrowven ORCID iD
Author: J. D. Wilden
Author: M. J. Tyte
Author: S. J. Coles ORCID iD

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