Syntheses of Epimeric 2- and 4-Deuteriocholesterols

Syntheses of Epimeric 2- and 4-Deuteriocholesterols

In order to clarify the stereochemistry of hydrogen loss from C-2 and C-4 during microbial transformation of cholesterol into androsta-1, 4-diene-3, 17-dione, the stereospecific syntheses of epimeric 2- and 4-deuteriocholesterols (XIII, XVI, XIX, XXI) have been undertaken. The key intermediates lead...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1974/11/25, Vol.22(11), pp.2656-2661
Hauptverfasser: NAMBARA, TOSHIO, IKEGAWA, SHIGEO, ISHIZUKA, TSUYAKO, GOTO, JUNICHI
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container_end_page 2661
container_issue 11
container_start_page 2656
container_title Chemical & pharmaceutical bulletin
container_volume 22
creator NAMBARA, TOSHIO
IKEGAWA, SHIGEO
ISHIZUKA, TSUYAKO
GOTO, JUNICHI
description In order to clarify the stereochemistry of hydrogen loss from C-2 and C-4 during microbial transformation of cholesterol into androsta-1, 4-diene-3, 17-dione, the stereospecific syntheses of epimeric 2- and 4-deuteriocholesterols (XIII, XVI, XIX, XXI) have been undertaken. The key intermediates leading to the required substrates, Δ2- and Δ3-5α-cholesten-5-ols (II, VIII), were prepared from cholesterol in several steps. These olefins were converted to the 2α- and 4α-deuterio-3α, 5α-diols (XI, XVII) by treatment with deuteriodiborane. On the other hand trans-diaxial opening of the α-epoxides (III, Vb) with lithium aluminum deuteride provided the 2β-and 4β-deuterio-3, 5α-diols (XIV, XX). Upon dehydration with thionyl chloride and pyridine these labeled products were led to the desired compounds.
doi_str_mv 10.1248/cpb.22.2656
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title Syntheses of Epimeric 2- and 4-Deuteriocholesterols
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