Synthesis of the Ring  D ‐Building Block of (24 S )‐24‐Hydroxy Vitamin D 3  from Menthol, I | Zendy

Daniewski Andrzej Robert | Zendy; Warchol Tadeusz | Zendy

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Synthesis of the Ring D ‐Building Block of (24 S )‐24‐Hydroxy Vitamin D 3 from Menthol, I

Author(s) -

Daniewski Andrzej Robert,

Warchol Tadeusz

Publication year - 1992

Publication title -

liebigs annalen der chemie

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0170-2041

DOI - 10.1002/jlac.1992199201159

Subject(s) - chemistry , menthol , epoxide , vitamin , bromide , alkylation , natural product , block (permutation group theory) , ring (chemistry) , lactone , organic chemistry , medicinal chemistry , biochemistry , geometry , mathematics , catalysis

Natural (—)‐menthol ( 4 ) was oxidized to the lactone 9 which was alkylated with allyl bromide to a single product 10 . The latter compound was transformed into bromo epoxide 33 which was cyclized with the highly reactive copper to the desired ring D Building block 18 of (24 S )‐24‐hydroxy vitamin D 3 . The title compound 18 was synthesized also by free‐radical cyclization of enaldehyde 40 .

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