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Synthesis of a trans ‐Hydrindanone, Precursor for the Preparation of Vitamin D Analogues
Author(s) -
Gándara Zoila,
Rivadulla Marcos L.,
Pérez Manuel,
Gómez Generosa,
Fall Yagamare
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300528
Subject(s) - synthon , chemistry , ketone , calcitriol , derivative (finance) , stereochemistry , vitamin d and neurology , vitamin , ring (chemistry) , combinatorial chemistry , organic chemistry , biochemistry , calcium , medicine , endocrinology , financial economics , economics
We developed a very efficient and practical method for the large‐scale synthesis of a trans ‐hydrindan derivative related to vitamin D, based on the Criegee rearrangement. This ketone is a valuable synthon for the preparation of Gemini‐type vitamin D analogues or other calcitriol analogues modified at C‐20, C‐21 or the D‐ring. Our methodology is superior to those previously reported when considering efficiency and expediency.