The Synthesis of the Precursor of the Bicyclic--Enediyne 6-Sulfony-13-oxo-bicyclo[9.3.0]-tetradec-3,8-diyne(Ⅱ)

Chem. J. Chinese Universities ›› 1999, Vol. 20 ›› Issue (12): 1888.

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The Synthesis of the Precursor of the Bicyclic--Enediyne 6-Sulfony-13-oxo-bicyclo[9.3.0]-tetradec-3,8-diyne(Ⅱ)

ZHI Yong-Gang¹, TENG You-Wei¹, ZHANG Liang-Fu¹, Just-George²

1. Chengdu Organic Chemistry Institute of Chinese Academy of Sciences, Chengdu 610041, China;
2. Department of Chemistry, McGill University, H3A 2K6, Canada

Received:1999-04-08 Online:1999-12-24 Published:1999-12-24

Abstract

Abstract: 6-Sulfony-13-oxybicyclo[9.3.0]tetradec-3,8-diyne is the precursor of the bicyclic enediyne which has been synthesized from cis-1,2,3,6-tetrahydropathalican hydride by 8-step reactions. We got the goal compound by reduction of anhydride, ozonolysis of 8-oxabicyclo[4.3.0]non-3-ene, Witting reaction with PPh₃/CBr₄, formation of alkyne and esterification, reduction of the ester, formation of the mesylate, cyclization with sodium sulfide nonhydrate. The structures of new compounds 4_9 have been identified by elementary analysis, NMR, IRand MS spectra.

Key words: Heterocyclic compound, Cyclo-1,5-diyne-3-ene, Anticancer antibiotics

CLC Number:

O626

TrendMD:

ZHI Yong-Gang, TENG You-Wei, ZHANG Liang-Fu, Just-George . The Synthesis of the Precursor of the Bicyclic--Enediyne 6-Sulfony-13-oxo-bicyclo[9.3.0]-tetradec-3,8-diyne(Ⅱ)[J]. Chem. J. Chinese Universities, 1999, 20(12): 1888.

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The Synthesis of the Precursor of the Bicyclic--Enediyne 6-Sulfony-13-oxo-bicyclo[9.3.0]-tetradec-3,8-diyne(Ⅱ)

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