Issue 10, 1977
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Calciferol and its relatives. Part 19. Synthetic applications of cyclic orthoesters: stereospecific synthesis of a bicyclic alcohol related to the vitamins D2

Christopher B. Chapleo,   Peter Hallett,   Basil Lythgoe,   Ian Waterhouse  and  Paul W. Wright  

Abstract

Examples are described of Claisen rearrangements using cyclic orthoesters. Their synthetic potential is pointed out and illustrated by a synthesis of the optically active 1β-[(R)-2-hydroxy-1-methylethyl]-3aα,6,7,7aβ-tetrahydro-7aβ-methylindane (31), a compound intended as an intermediate for syntheses of vitamin D2 and 25-hydroxyvitamin D3. In the key reaction between 2-hydroxy-4-methylcyclohex-3-enyl benzoate (7) and 2,2-diethoxy-4-methyltetrahydrofuran (24) the asymmetric centre C-1 of the final product (31) is set up stereospecifically by asymmetric induction with the required configuration, and this configuration is maintained throughout the synthesis.

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Article information

DOI
https://doi.org/10.1039/P19770001211
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1977, 1211-1218

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Calciferol and its relatives. Part 19. Synthetic applications of cyclic orthoesters: stereospecific synthesis of a bicyclic alcohol related to the vitamins D2

C. B. Chapleo, P. Hallett, B. Lythgoe, I. Waterhouse and P. W. Wright, J. Chem. Soc., Perkin Trans. 1, 1977, 1211 DOI: 10.1039/P19770001211

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