C50 Carotenoids. 18. Syntheses and Chirality of Aliphatic C50 Carotenoids.
- 1 January 1979
- journal article
- research article
- Published by Danish Chemical Society in Acta Chemica Scandinavica
- Vol. 33b (8), 551-558
- https://doi.org/10.3891/acta.chem.scand.33b-0551
Abstract
Details regarding total syntheses of (2R,2''R)-tetradeoxybacterioruberin (13) and (2S,2''S)-tetraanhydrobacterioruberin (18) from (-)-lavandulol (3) are given. A low yield synthesis of optically inactive bacterioruberin is reported. Formation of octanor by-products in the final Wittig condensation to C50-carotenoids with crocetindial, ascribed to the elimination of toluene, is rationalized on a mechanistic basis. Chiroptical correlation of 18, obtained by dehydration of natural bacterioruberin (1) and of natural bisanhydrobacterioruberin (2) with synthetic 18, proved the 2S,2''S-configuration for 1 and 2. Synthetic 13 was not a valid CD-model. Total syntheses of aliphatic C50-carotenoids and chiroptical correlations revealing the absolute configuration of 1 and of 2, Scheme 1, were reported.This publication has 4 references indexed in Scilit:
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