124388-95-0Relevant articles and documents
Total Synthesis of (2S,3S,4R)-2--16-methylheptadecane-1,3,4-triol 3,4-dibenzoate, a Partially Protected Ceramide Part of Sponge Cerebrosides
Nakashima, Hideki,Hirata, Norihiko,Iwamura, Takeru,Yamagiwa, Yoshiro,Kamikawa, Tadao
, p. 2849 - 2858 (1994)
(2S,3S,4R)-2--16-methylheptadecane-1,3,4-triol 3,4-dibenzoate 32, apertially protected ceramide part of a cerebroside from the marine sponge Halichondria japonica, has been synthesized from L-ascorbic acid, and its absolute stereochemistry has been determined.The key steps in the synthesis include the regioselective ring opening of chiral epoxide 5 with a 2-alkyl-2-lithio-1,3-dithiane and the introduction of a hydroxymethylene synthon using Dondoni's protocol to assemble C(1) and C(2) functionality.
An asymmetric synthesis of sulfobacin A
Sharma, Anubha,Gamre, Sunita,Chattopadhyay, Subrata
, p. 3705 - 3707 (2008/02/09)
A facile synthesis of sulfobacin A has been developed starting from (R)-cyclohexylideneglyceraldehyde (11). The key steps in the synthesis are the highly diastereocontrolled allylation of 11 and syn-selective reduction of a ketone derived from 11. The oth
Synthesis of 14-methylpentadecan-3-one and 2-methylheptadecane
Kad, G. L.,Gupta, Sangita
, p. 581 - 583 (2007/10/02)
Li2CuCl4 catalysed coupling of 1-tetrahydropyranyloxy-8-octanylmagnesium bromide (III) with isobutyl bromide yields IV which on depyranylation with PPTS/MeOH followed by treatment with PBr3 affords the key intermediate 1-bromo-10-methylundecane (VI).Regioselective alkylation of α-lithio-2-butanone N,N-dimethylhydrazone with VI in THF at -78 deg C followed by oxidative hydrolysis with aq.NaIO4 at pH 7 results in the formation of 14-methylpentadecan-3-one (I).Coupling of VI with hexylmagnesium bromide using Li2CuCl4 as catalyst furnishes the target compound (II).