180865-96-7

Upstream product

• 5056-07-5 (S)-methyl p-tolyl sulfoxide 
• 74510-49-9 [5-((E)-4-Bromo-2-methyl-but-2-enyl)-2-chloro-3-methoxy-phenyl]-methyl-carbamic acid methyl ester 

Downstream Products

• 1053634-29-9 C₄₆H₇₈ClNO₁₀S₂Si 
• 1055038-19-1 (E)-(3S,6S,7S)-3-(tert-Butyl-dimethyl-silanyloxy)-8-(2-{(2E,4E)-(R)-6-[4-chloro-3-methoxy-5-(methoxycarbonyl-methyl-amino)-phenyl]-1-methoxy-5-methyl-hexa-2,4-dienyl}-[1,3]dithian-2-yl)-7-(2-methoxy-ethoxymethoxy)-4,6-dimethyl-oct-4-enoic acid 
• 1053749-61-3 [2-Chloro-5-((2E,4E)-(R)-6-{2-[(E)-(2S,3S,6S)-8,8-diethoxy-6-hydroxy-2-(2-methoxy-ethoxymethoxy)-3,5-dimethyl-oct-4-enyl]-[1,3]dithian-2-yl}-6-methoxy-2-methyl-hexa-2,4-dienyl)-3-methoxy-phenyl]-methyl-carbamic acid methyl ester 
• 75340-63-5 (E)-(3S,6S,7S)-3-(tert-Butyl-dimethyl-silanyloxy)-8-{2-[(2E,4E)-(R)-6-(4-chloro-3-methoxy-5-methylamino-phenyl)-1-methoxy-5-methyl-hexa-2,4-dienyl]-[1,3]dithian-2-yl}-7-(2-methoxy-ethoxymethoxy)-4,6-dimethyl-oct-4-enoic acid 
• 1054654-60-2 (E)-(3S,6S,7S)-8-(2-{(2E,4E)-(R)-6-[4-Chloro-3-methoxy-5-(methoxycarbonyl-methyl-amino)-phenyl]-1-methoxy-5-methyl-hexa-2,4-dienyl}-[1,3]dithian-2-yl)-3-hydroxy-7-(2-methoxy-ethoxymethoxy)-4,6-dimethyl-oct-4-enoic acid 
• 57103-68-1 (-)-maytansinol 
• 1053627-73-8 C₄₅H₇₆ClNO₁₀S₂Si 

Relevant academic research and scientific papers

Total synthesis of (-)-maytansinol

A total synthesis of maytansinol (1) was achieved, in a convergent way, using (3S,6S,7S)-aldehyde 4 and (S)-p-tolyl sulfoxide 3 as fragments. When the anion of 3 was condensed with aldehyde 4, some induction at C(10) was observed (60% de), giving the C(1)-N(19)-open-chain compound 7, after thermal elimination of sulfinate. Pure E/E stereochemistry of the 11,13-diene was obtained. Selective modifications of the functionalities permitted macrocyclization and further elaboration to maytansinol.