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Clemmensen reduction of diosgenin and kryptogenin: synthesis of [16,16,22,22,23,23-2H6]-(25R)-26-hydroxycholesterol

✍ Scribed by Laura Alessandrini; Pierangela Ciuffreda; Enzo Santaniello; Giancarlo Terraneo

Book ID
116891741
Publisher
Elsevier Science
Year
2004
Tongue
English
Weight
99 KB
Volume
69
Category
Article
ISSN
0039-128X

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πŸ“œ SIMILAR VOLUMES

Synthesis of kryptogenin-26-14C and dios
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Kryptogenin-26-I4C (13) was synthesized from dihydrodiosgenin diacetate (1). The radioactive carbon atom was introduced by the Arndt-Eistert method, and the extra carbon atom was then removed by a carboxy-inversion reaction. Diosgenin-26-I4C (14) was prepared by reduction of kryptogenir~-26-~~C.

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Four major byproducts qf the Clcmmensen reduction of diosgwdn have ken isolated and kienti\_Red: (2SR)-l7fi mcthyl-18-~r-17~cholesta-5.13-~~-3~~6-~1. dihydrodiosgenin, (22E~SR)-choiesta-522-dicncJs.16B26-ui, and its 222 isomer. These bproducts were used to prepare deuteriwn-and tritium4abeled (2SR)-