884869-08-3

Upstream product

• 2960-66-9 4-oxo-but-2-enoic acid ethyl ester 
• 21573-31-9 oct-7-enal 
• 13175-44-5 oct-7-en-1-ol 
• 884869-05-0 ethyl (2E,5Z)-6-[2-[(S)-6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]heptyl]-1,3-dioxolan-2-yl]-4-hydroxy-2,5-hexadienoate 
• 884869-03-8 ethyl (E)-6-[2-[(S)-6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]heptyl]-1,3-dioxolan-2-yl]-4-hydroxy-2-hexen-5-ynoate 
• 884868-95-5 (S)-(1,1-dimethylethyl)[[6-(2-ethynyl-1,3-dioxolan-2-yl)-1-methylhexyl]oxy]dimethylsilane 
• 884869-16-3 (R)-2-ethynyl-2-(5-oxiranylpentyl)-1,3-dioxolane 
• 884869-17-4 1-(trimethylsilyl)-9-decen-1-yn-3-ol 
• 884868-97-7 1-(trimethylsilyl)-9-decen-1-yn-3-one 
• 884869-01-6 (S)-7-(2-ethynyl-1,3-dioxolan-2-yl)-2-heptanol 
• 884868-99-9 (+/-)-2-ethynyl-2-(5-oxiranylpentyl)-1,3-dioxolane 
• 884868-98-8 2-ethynyl-2-(6-heptenyl)-1,3-dioxolane 

Downstream Products

• 884869-09-4 (2E,5Z)-6-[[2-[(S)-6-hydroxy]heptyl]-1,3-dioxolan-2-yl]-4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2,5-hexadienoic acid 

Relevant academic research and scientific papers

Synthesis of (+)-Sch 642305 by a biomimetic transannular Michael reaction

The synthesis of (+)-Sch 642305 (1) has been completed in 17 steps in 1.6% overall yield. Transannular Michael reaction of 2b with NaH in THF provided cyclohexenone 23 stereospecifically. Heating 23 in TFA/CDCI3 provided a 3:1 equilibrium mixture of 23 and 25, which was hydrolyzed to give (+)-6-epi-Sch 642305 (24) and (+)-Sch 642305 (1), respectively.