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Volumn 32, Issue 20, 1991, Pages 2269-2272

Milbemycin synthesis: synthesis of 6β-hydroxy-3,4-dihydromilbemycin E

Author keywords

furan oxidation; macrocyclisation; Milbemycin; Robinson annelation; spiroacetal.

Indexed keywords

3,4 DIHYDRO 6BETA HYDROXYMILBEMYCIN E; ANTHELMINTIC AGENT; MILBEMYCIN G; UNCLASSIFIED DRUG;

EID: 0025735747     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)79699-7     Document Type: Article
Times cited : (13)

References (19)
  • 12
    • 85007766195 scopus 로고
    • Total Synthesis of Avermectin B1a: Final Coupling Reactions and the Total Synthesis of Avermectin B1a Aglycone
    • (1990) Synlett , pp. 328
    • Armstrong1    Ley2    Madin3    Mukherjee4
  • 17
    • 84914295946 scopus 로고    scopus 로고
    • This reaction was found to be sensitive to solvent; for example in a 50:50 mixture of ethanol and dichloromethane, (1) and (ii) together with the open chain intermediates (iii) were isolated in addition to (6). The structure of the Robinson products, and the reduction products obtained from them, were established by extensive n.m.r. studies. Details will be given in a full paper.
  • 18
    • 84914295945 scopus 로고    scopus 로고
    • The work in this paper involved the use of racemic Robinson annelation products, and hence gave the mixture of Wittig products. However resolution of the diol (10) has been achieved by esterification using (S)-acetoxymandelic acid to give (iv) and (v), and selective crystallization of the required diasteroisomer (iv). Hydrogenation of the acetoxymandelates proceeds with concomitant hydrogenolysis of both the benzyl ether and the acetoxy group to give the hydroxyphenylacetate (11).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.