Ag. Martinez et al., From natural camphor to (1R,2S)-2-chloromethyl-3-oxocyclopentanecarboxylicacid: a stereocontrolled approach to enantiopure sarkomycin, TETRAHEDR L, 42(44), 2001, pp. 7795-7799
The preparation of enantiopure (1R,2S)-2-chloromethyl-3-oxocyclopentanecarb
oxylic acid 9. an interesting possible precursor of the antitumor agent sar
komycin, from a camphor-derived 3-hydroxymethylorbornan-2-one is reported.
The described procedure Constitutes the fil-st stereocontrolled approach to
sarkomycin starting from commercially available natural camphor. The proce
dure takes place in only six steps with a high overall yield (59%). The key
-step of the described procedure is the stereocontrolled ring opening of a
conveniently functionalized 3-oxonorborn-1-yl triflate under a straightforw
ard basic hydrolysis. The described route constitutes a model procedure for
the preparation of other enantiopure C2-substituted 3-oxocyclopentanecarbo
xylic acids, which are related with the sarkomycin family of antitumor agen
ts. (C), 2001 Elsevier Science Ltd. All rights reserved.