723296-13-7

Upstream product

• 131216-47-2 5-(tert-butyldiphenylsilyloxy)pentanal 
• 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 
• 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 
• 723296-06-8 1-(tert-butyldiphenylsilyloxy)-7-methyl-non-8-en-5-ol 
• 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 
• 111-29-5 1 ,5-pentanediol 
• 946408-87-3 (4R)-8-tert-butyldiphenylsilyloxy-1-octen-4-ol 
• 946408-85-1 (3S,5R)-9-tert-butyldiphenylsilyloxy-3-methyl-1-nonen-5-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 
• 1246367-21-4 C₂₆H₄₀INO₃ 

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.

An asymmetric hydrogenation route to (-)-Spongidepsin

Figure Presented. (-)-Spongidepsin 1, a cytotoxic marine natural product, was prepared via two iridium-catalyzed hydrogenation reactions; both were highly stereoselective, giving convenient access to pivotal intermediates. This synthesis was modified to g

Formal total synthesis of (-)-spongidepsin

The formal total synthesis of (-)-spongidepsin is described. Three fragments I, II, and III were first prepared from readily available starting materials and then assembled to the target compound. The key steps involved in the synthesis are asymmetric α-hydroxylation, Ender's alkylation, and ring-closing metathesis reactions. An alternative route for the fragment II is also achieved involving Sharpless asymmetric epoxidation and Gilman's alkylation as key reactions.

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

Stereoselective formal total synthesis of the cyclodepsipeptide (-)-spongidepsin

The formal total synthesis of (-)-spongidepsin is achieved starting from easily available raw materials involving asymmetric α-hydroxylation, Enders alkylation, and RCM as key reactions.

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%.