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《Acta Chimica Sinica》 1984-08
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LIN GUO-QIANG~* WU BI-CHI LIU LIN-YU WANG XIAN-QING ZHOU WEI-SHAN(Shanghai Institute of Organic Chemistry Academia Sinica)  
The title compounds 1a~d were synthesized from(+)-(R)-glyceraldehyde acetonide (2) obtained from mannitol in 9~10 steps in an overall yield of 20~30%. Thus, Grignard reaction of 2 with n-C_(10)H_(21)MgBr yielded a mixture of two diastereoisomers which afforded 3(erythro form, R, S) and 4 (threo form, R, R) by SiO_2 gel chromatography. The free alcohol 3 was reacted with benzyl chloride followed by acidic hydrolysis to give diol 6 which on selective tosylation followed by treatment with 0.25 M methanolic KOH gave an epoxide 8. 8 was treated with(i-hex)_2 OuLi in ether to give 9 which on removal of the benzyl protecting group followed by reaction with HBr-HOAc gave a mixture of 11a and 11b. Finally, treatment of the mixture of 11a and 11b with 0.5M methanolic KOH gave (+)-disparlure(1a). 1c and 1d were obtained from 9 by the reaction sequences as shown in the Chinese Text. The (-)-disparlure (1b) was obtained from 4 by the reaction sequences of 5'→6'→7'→8'→9'→1b.
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