PREPARATION OF 7,8,16-TRIHYDROXY-HEXADECANOIC ACID FROM ALEURITIC ACID AND A SYNTHESIS OF E Z-7-HEXADECEN-1,16-OLIDES AND HEXALURE/

Authors
TEWARI N ROHATGI A BHUSHAN KH SUBRAMANIAN GBV
Citation
N. Tewari et al., PREPARATION OF 7,8,16-TRIHYDROXY-HEXADECANOIC ACID FROM ALEURITIC ACID AND A SYNTHESIS OF E Z-7-HEXADECEN-1,16-OLIDES AND HEXALURE/, Indian journal of chemistry. Sect. B: organic chemistry, including medical chemistry, 34(10), 1995, pp. 851-855
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Indian journal of chemistry. Sect. B: organic chemistry, including medical chemistry → ACNP
ISSN journal
03764699
Volume
34
Issue
10
Year of publication
1995
Pages
851 - 855
Database
ISI
SICI code
0376-4699(1995)34:10<851:PO7AFA>2.0.ZU;2-8
Abstract
Both threo/erythro 7,8,16-trihydroxy-hexadecanoic acids have been prep ared from threo/erythro 9,10,16-trihydroxy-hexadecanoic acids (aleurit ic acid), by interchanging the positions of the terminal carboxyl and hydroxyl groups through steps of appropriate oxidation-reduction on th e dithianes obtained from the 16-oxo-9,10-dihydroxy-hexadecanoic acids . Cyclization of the corresponding 9,10-olefin with dibutyl tin oxide furnish E/Z-7-hexadecen-1,16-olides. Preparation of the insect pheromo ne hexalure is also reported.