328404-70-2

Upstream product

• 95456-65-8 (1R,5R)-(-)-6-aza-6-benzyloxycarbonyl-2-oxabicyclo[3.3.0]octan-3-one 
• 389874-45-7 3-(tert-butyl-diphenyl-silanyloxy)-2-[1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyl]-pyrrolidine-1-carboxylic acid benzyl ester 
• 328404-68-8 3-(tert-butyl-diphenyl-silanyloxy)-2-[1-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-propyl]-pyrrolidine-1-carboxylic acid benzyl ester 
• 328404-66-6 (3R)-1-(benzyloxycarbonyl)-3-hydroxy-2-[2-(4-pentenyl-1-ol)]pyrrolidine 
• 328404-64-4 (1R,4R,5R)-6-(benzyloxycarbonyl)-4-(3-propenyl)-6-aza-2-oxa-bicyclo[3.3.0]-3-octanone 
• 328404-56-4 (R)-3-[(1-bezyloxy-carbonyl)-pyrrolidinyl]-α-diazoacetate 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 328404-69-9 3-(tert-butyl-diphenyl-silanyloxy)-2-[1-(tert-butyl-diphenyl-silanyloxymethyl)-3-methanesulfonyloxy-propyl]-pyrrolidine-1-carboxylic acid benzyl ester 

Downstream Products

• 21850-67-9 (-)-turneforcidine 

Relevant academic research and scientific papers

A dirhodium(II)-carbenoid route to (-)- and (+)-Geissman-Waiss lactone: Synthesis of (1R,7R,8R)-(-)-turneforcidine

(-)- and (+)-Geissman-Waiss lactone, 4b, was efficiently prepared via the intramolecular C-H insertion reaction of the chiral nonracemic diazoacetates (-)-5a and (+)-5b catalyzed by dirhodium(II) tetrakis[methyl (5R and 5S)-3-phenylpropanoyl-2-imidazolidinone-5-carboxylate]. The cyclization was found to proceed with excellent regioselectivity and cis-diastereoselectivity. The bicyclic lactone (-)-4b was successfully used in the synthesis of the necine base, (-)-turneforcidine 2.

A facile synthesis of (-)- and (+)-Geissman-Waiss lactone via intramolecular Rh(II)-carbenoid mediated C-H insertion reaction: Synthesis of (1R,7R,8R)-turneforcidine

The intramolecular C-H insertion reaction in chiral non-racemic diazoacetates (-)-6 and (+)-8 catalyzed by chiral Rh2(MPPIM)4 proceeded efficiently, with excellent regioselectivity and cis-diastereoselectivity, to give (-)- and (+)-G