277749-83-4

Upstream product

• 7540-51-4 (S)-3,7-dimethyl-6-octen-1-ol 
• 1352710-58-7 (4S)-6-bromo-4-methylhexan-1-ol 
• 41144-01-8 (S)-3,7-dimethyl-6-octenyl tosylate 
• 10340-84-8 (S)-citronellyl bromide 
• 5949-05-3 (S)-Citronellal 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 885218-74-6 (S)-2-Methyl-5-trityloxy-pentanal 
• 1027040-40-9 (S)-1-bromo-3-methyl-6-(triphenylmethyl)oxyhexane 
• 277749-82-3 (S)-3-methyl-6-(triphenylmethyl)oxyhex-1-ene 
• 312619-58-2 (S)-6-Bromo-4-methyl-hexanal 

Downstream Products

• 277749-84-5 (2E,4S)-1-benzyloxy-4-methyl-7-(triphenylmethyl)oxyhept-2-ene 
• 277749-86-7 (4S,5S,6R)-7-benzyloxy-6-iodo-4-methylheptan-5-olide 

Relevant academic research and scientific papers

Synthesis of the spiroacetal fragments of spirofungins A and B, antibiotics isolated from Streptomyces violaceusniger Tü 4113

The spiroacetal [C(9)-C(20)] fragments of spirofungins A and B, antibiotics isolated from Streptomyces violaceusniger Tü 4113, were prepared from a known bromo alcohol derived from (S)-citronellal, using thermodynamically controlled iodolactonization and spiroacetalization as the key steps.

Synthesis of the spiroacetal parts of spirofungin A and B

The C9-C20 spiroacetal parts of spirofungin A and B, antifungal antibiotics from Streptomyces violaceusniger Tu 4113, were synthesized simultaneously from (S)-citronellyl bromide and (±)-epoxy alcohol via alkyne-lactone coupling reaction and diastereomeric separation. (C) 2000 Elsevier Science Ltd.