723296-05-7

Upstream product

• 723296-06-8 1-(tert-butyldiphenylsilyloxy)-7-methyl-non-8-en-5-ol 
• 723296-11-5 2-(tert-butoxycarbonyl-methyl-amino)-3-phenyl-propionic acid 1-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-3-methyl-pent-4-enyl ester 
• 116179-61-4 (2R,4R)-2,4-dimethyl-hex-5-enoic acid 
• 106357-27-1 (2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2,4-dimethyl-hex-5-en-3-ol 
• 37553-65-4 Boc-N-Me-Phe-OH 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 908357-56-2 Methanesulfonic acid (1S,2R)-1-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2-methyl-but-3-enyl ester 
• 454482-21-4 (2R,4R)-2,4-dimethyl-hex-5-en-1-ol 
• 147782-81-8 (2S,4R)-1-<(tert-Butyldimethylsilyl)oxy>-2,4-dimethylpentanal 
• 147782-80-7 (2S,4R)-5-(tert-butyl(dimethyl)silyloxy)-2,4-dimethyl-1-pentanol 
• 121671-76-9 5-(tert-butyldiphenylsilyloxy)pentan-1-ol 
• 131216-47-2 5-(tert-butyldiphenylsilyloxy)pentanal 
• 111-29-5 1 ,5-pentanediol 
• 946408-87-3 (4R)-8-tert-butyldiphenylsilyloxy-1-octen-4-ol 

Downstream Products

• 713143-96-5 4-((3S,6R,8R,11R,13R)-3-Benzyl-4,6,8,11-tetramethyl-2,5-dioxo-1-oxa-4-aza-cyclotridec-13-yl)-butyraldehyde 
• 723296-19-3 (Z)-(3S,6R,8S,11S,13R)-3-Benzyl-13-(4-hydroxy-butyl)-4,6,8,11-tetramethyl-1-oxa-4-aza-cyclotridec-9-ene-2,5-dione 
• 723296-12-6 (Z)-(3S,6R,8S,11S,13R)-3-Benzyl-13-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-4,6,8,11-tetramethyl-1-oxa-4-aza-cyclotridec-9-ene-2,5-dione 

Relevant academic research and scientific papers

Enantioselective syn and anti homocrotylation of aldehydes: Application to the formal synthesis of spongidepsin

Whereas crotylboration has been a useful method for synthesis of stereochemically complex products, we have shown that homocrotylboration can be achieved with cyclopropanated crotylation reagents, and that the stereoselectivity of the reaction can be predicted by analogous models. This paper presents a full account of this work, including the first examples of asymmetric anti homocrotylation. The scope of this reaction is demonstrated with highly enantioselective homocrotylation of both aliphatic and aromatic aldehydes, as well as double diastereoselection studies. An application of the synthesis of the marine natural product spongidepsin is presented, as well as streamlined syntheses of homocrotylation reagents.

Fully reagent-controlled asymmetric synthesis of (-)-Spongidepsin via the Zr-catalyzed asymmetric carboalumination of alkenes (ZACA reaction)

The ZACA reaction has been shown to proceed satisfactorily with internally OH-substituted 1-alkenes, provided that the OH group is unprotected and non-allylic. This reaction was used for reagent-controlled asymmetric construction of 3. Allylic alcohol was

Total synthesis of (-)-spongidepsin

A convergent and rapid stereoselective synthesis of (-)-spongidepsin has been achieved from the Roche ester in 14 steps with an overall yield of 13%.