CHEMISTRY OF INSECT ANTIFEEDANTS FROM AZADIRACHTA-INDICA .13. ON THE USE OF THE INTRAMOLECULAR DIELS-ALDER REACTION FOR THE CONSTRUCTION OF TRANS-FUSED HYDROBENZOFURAN FRAGMENTS FOR AZADIRACHTIN SYNTHESIS

H C  KOLB; S V  LEY; R N  SHEPPARD; A M Z  SLAWIN; S C  SMITH; D J  WILLIAMS; A  WOOD

CHEMISTRY OF INSECT ANTIFEEDANTS FROM AZADIRACHTA-INDICA .13. ON THE USE OF THE INTRAMOLECULAR DIELS-ALDER REACTION FOR THE CONSTRUCTION OF TRANS-FUSED HYDROBENZOFURAN FRAGMENTS FOR AZADIRACHTIN SYNTHESIS

H C KOLB, S V LEY, R N SHEPPARD, A M Z SLAWIN, S C SMITH, D J WILLIAMS, A WOOD

Research output: Contribution to journal › Article › peer-review

Abstract

This paper describes a detailed analysis of the influence of various substituents on the stereochemical outcome of the intramolecular Diels-Alder cyclisation of a number of ether-linked trienes. In particular, the role of diene planarity in governing reaction synchronicity and related twist asynchronicity is delineated. Additionally, the controlling influence of a large dimethyl(phenyl)silyl substituent on the dienophile portion of the triene is also explored. A detailed transition-state analysis is given together with X-ray structures for compounds 41 and 46.

Original language	English
Pages (from-to)	2763-2777
Number of pages	15
Journal	Journal of the Chemical Society, Perkin Transactions 1
Issue number	21
Publication status	Published - 7 Nov 1992

Keywords

STEREOCHEMICAL ASPECTS
NMR

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KOLB, H. C., LEY, S. V., SHEPPARD, R. N., SLAWIN, A. M. Z., SMITH, S. C., WILLIAMS, D. J., & WOOD, A. (1992). CHEMISTRY OF INSECT ANTIFEEDANTS FROM AZADIRACHTA-INDICA .13. ON THE USE OF THE INTRAMOLECULAR DIELS-ALDER REACTION FOR THE CONSTRUCTION OF TRANS-FUSED HYDROBENZOFURAN FRAGMENTS FOR AZADIRACHTIN SYNTHESIS. Journal of the Chemical Society, Perkin Transactions 1, (21), 2763-2777.

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title = "CHEMISTRY OF INSECT ANTIFEEDANTS FROM AZADIRACHTA-INDICA .13. ON THE USE OF THE INTRAMOLECULAR DIELS-ALDER REACTION FOR THE CONSTRUCTION OF TRANS-FUSED HYDROBENZOFURAN FRAGMENTS FOR AZADIRACHTIN SYNTHESIS",

abstract = "This paper describes a detailed analysis of the influence of various substituents on the stereochemical outcome of the intramolecular Diels-Alder cyclisation of a number of ether-linked trienes. In particular, the role of diene planarity in governing reaction synchronicity and related twist asynchronicity is delineated. Additionally, the controlling influence of a large dimethyl(phenyl)silyl substituent on the dienophile portion of the triene is also explored. A detailed transition-state analysis is given together with X-ray structures for compounds 41 and 46.",

keywords = "STEREOCHEMICAL ASPECTS, NMR",

author = "KOLB, {H C} and LEY, {S V} and SHEPPARD, {R N} and SLAWIN, {A M Z} and SMITH, {S C} and WILLIAMS, {D J} and A WOOD",

year = "1992",

month = nov,

day = "7",

language = "English",

pages = "2763--2777",

journal = "Journal of the Chemical Society, Perkin Transactions 1",

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KOLB, HC, LEY, SV, SHEPPARD, RN, SLAWIN, AMZ, SMITH, SC, WILLIAMS, DJ & WOOD, A 1992, 'CHEMISTRY OF INSECT ANTIFEEDANTS FROM AZADIRACHTA-INDICA .13. ON THE USE OF THE INTRAMOLECULAR DIELS-ALDER REACTION FOR THE CONSTRUCTION OF TRANS-FUSED HYDROBENZOFURAN FRAGMENTS FOR AZADIRACHTIN SYNTHESIS', Journal of the Chemical Society, Perkin Transactions 1, no. 21, pp. 2763-2777.

CHEMISTRY OF INSECT ANTIFEEDANTS FROM AZADIRACHTA-INDICA .13. ON THE USE OF THE INTRAMOLECULAR DIELS-ALDER REACTION FOR THE CONSTRUCTION OF TRANS-FUSED HYDROBENZOFURAN FRAGMENTS FOR AZADIRACHTIN SYNTHESIS. / KOLB, H C ; LEY, S V ; SHEPPARD, R N et al.
In: Journal of the Chemical Society, Perkin Transactions 1, No. 21, 07.11.1992, p. 2763-2777.

Research output: Contribution to journal › Article › peer-review

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AU - KOLB, H C

AU - LEY, S V

AU - SHEPPARD, R N

AU - SLAWIN, A M Z

AU - SMITH, S C

AU - WILLIAMS, D J

AU - WOOD, A

PY - 1992/11/7

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N2 - This paper describes a detailed analysis of the influence of various substituents on the stereochemical outcome of the intramolecular Diels-Alder cyclisation of a number of ether-linked trienes. In particular, the role of diene planarity in governing reaction synchronicity and related twist asynchronicity is delineated. Additionally, the controlling influence of a large dimethyl(phenyl)silyl substituent on the dienophile portion of the triene is also explored. A detailed transition-state analysis is given together with X-ray structures for compounds 41 and 46.

AB - This paper describes a detailed analysis of the influence of various substituents on the stereochemical outcome of the intramolecular Diels-Alder cyclisation of a number of ether-linked trienes. In particular, the role of diene planarity in governing reaction synchronicity and related twist asynchronicity is delineated. Additionally, the controlling influence of a large dimethyl(phenyl)silyl substituent on the dienophile portion of the triene is also explored. A detailed transition-state analysis is given together with X-ray structures for compounds 41 and 46.

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JF - Journal of the Chemical Society, Perkin Transactions 1

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