131413-97-3

Upstream product

• 131413-96-2 <2S(2R,4E,6S,7S)>-2-<2-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-5,7-dimethylnona-4,8-dienyl>oxirane 
• 135419-79-3 (1E,3S,4S)-1-bromo-2,4-dimethylhexa-1,5-dien-3-ol 
• 131413-95-1 (1E,3S,4S)-1-bromo-3-(tert-butyldiphenylsilyloxy)-2,4-dimethylhexa-1,5-diene 

Downstream Products

• 135419-83-9 (4R)-5-dehydroxy-3,4-dihydro-5-oxo-4-(phenylselenyl)-7,13-di-O-(trimethylsilyl)avermectin B₁a aglycone 
• 135419-83-9 (4S)-5-dehydroxy-3,4-dihydro-5-oxo-4-(phenylselenyl)-7,13-di-O-(trimethylsilyl)avermectin B₁a aglycone 
• 131441-49-1 (3E<2E,4S,5S,6E,8<2R,4S,6S,8R(S),9S>>,3aS,4S,7R,7aR)-7-(tert-butyldimethylsilyloxy)-3-<5-(tert-butyldimethylsilyloxy)-8-undec-10-en-2-yl>-4,6-dimethylocta-2,6-dienylidene>-4-... 
• 131441-50-4 (4S)-5-dehydroxy-3,4-dihydro-5-oxo-4-(phenylselenyl)-avermectin B₁a aglycone 
• 135419-80-6 <2R(2E,4S,5S),4S,6S,8R(S),9S>-2-<4-(tert-butyldiphenylsilyloxy)-3,5-dimethylhepta-2,6-dienyl>-9-methyl-8-(1-methypropyl)-1,7-dioxaspiro<5.5>undec-10-en-4-ol 
• 65195-55-3 avermectin B₁a 

Relevant academic research and scientific papers

Total Synthesis of the Anthelmintic Macrolide Avermectin B1a

A highly convergent total synthesis of the anthelmintic macrolide avermectin B1a is described.The key features of this synthesis include the introduction of the C(11)-C(15) portion by selective ring opening of a symmetrical 1,4-bis-epoxide 4 followed by reaction with the anion derived from the 3-methyl-2-(1-methylpropyl)-6-phenylsulphonylpyran 3 to afford the 'northern' C(11)-C(25) fragment 39.Coupling of the derived C(11)-C(25) aldehyde unit 42 with a C(1)-C(10) 'southern' fragment 2 was achieved via a novel deconjugative vinyl sulphone anion sequence.Macrolactonisation and subsequent introduction of the 3,4-double bond gave the aglycone portion 51.The oleandrosyloleandrose disaccharide was introduced by a novel silver-mediated coupling between the 5-acetylated aglycone 70 and the thiocarbonylimidazolide 69.Final deacetylation was accomplished using Super-Hydride to give the natural product 1.