185409-68-1

Upstream product

• 251641-16-4 (S)-5-Benzyloxy-3-triethylsilanyloxy-pentanoic acid ethyl ester 
• 19790-60-4 3-Benzyloxypropanal 
• 95112-81-5 (S)-ethyl 5-benzyloxy-3-hydroxypentanoate 
• 111322-01-1 (R)-1-benzyloxy-hex-5-en-3-ol 
• 79271-56-0 triethylsilyl trifluoromethyl sulfonate 
• 253185-01-2 (R)-{[1-(benzyloxy)hex-5-en-3-yl]oxy}triethylsilane 
• 64714-79-0 5-benzyloxy-3-oxo-pentanoic acid ethyl ester 
• 4799-68-2 3-benzyloxypropan-1-ol 

Downstream Products

• 185409-83-0 1,13-dibenzyloxy-3,11-di(triethylsilyloxy)-5-tert-butyldimethylsilyloxy-9-hydroxy-tridecan-7-one 
• 1026363-66-5 (3S,11S)-1,13-Bis-benzyloxy-5-hydroxy-3,11-bis-triethylsilanyloxy-9-trimethylsilanyloxy-tridecan-7-one 
• 185409-71-6 (4S,6S)-8-benzyloxy-4-hydroxy-6-(triethylsiloxy)-2-octanone 
• 185409-75-0 (4S,6S)-8-benzyloxy-4-(tert-butyldimethylsiloxy)-6-(triethylsiloxy)-2-octanone 
• 185409-77-2 C₄₇H₈₃BO₄Si₂ 
• 199857-49-3 (2S,4S,6R,8S,10S)-8-(2-benzyloxyethyl)-10-(t-butyldimethylsiloxy)-2-{2-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-allyl}-1,7-dioxaspiro[5.5]undecan-4-ol 
• 199857-50-6 (2S,4S,6R,8S,10S)-8-(2-benzyloxyethyl)-10-(t-butyldimethylsiloxy)-4-methyl-2-{2-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-allyl}-1,7-dioxaspiro[5.5]undecan-4-ol 
• 862379-33-7 (2S,6R,8S,10S)-8-(2-Benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-2-((R)-3-methyl-2-methylene-4-triisopropylsilanyloxy-butyl)-1,7-dioxa-spiro[5.5]undecan-4-one 
• 199857-48-2 (3S,5S,9S,11S)-1-benzyloxy-5-(t-butyldimethylsiloxy)-9-hydroxy-13-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-3,11-bis(triethylsiloxy)-tetradec-13-en-7-one 
• 251641-17-5 (S)-8-Benzyloxy-4-hydroxy-6-triethylsilanyloxy-octan-2-one 

Relevant academic research and scientific papers

The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: The AB-spiroacetal segment

The convergent synthesis of the C1-C15 AB-spiroacetal subunit 2 of altohyrtin A/spongistatin 1 (1) is described. This highly stereocontrolled synthesis relies on matched boron aldol reactions of chiral methyl ketones, under Ipc2BCl mediation, t

Synthetic spiroketal pyranes as potent anti-cancer agents

Novel tubulin binding compounds (SPIKETS) having potent tubulin depolymerization activity and inhibitory activity against tubulin polymerization. The compounds are effective agents for inhibiting cellular proliferation, for example, in cancer cells. The compounds are adapted to interact favorably with a novel SP binding pocket on tubulin, which pocket is useful for screening of anti-tubulin, anti-proliferation, and anti-cancer drugs.

Synthesis of the C1-C28 Portion of Spongistatin 1 (Altohyrtin A)

A synthetic approach was developed to the C1-C28 subunit of spongistatin 1 (altohyrtin A, 65). The key step was the coupling of the AB and CD spiroketal moieties via an anti-aldol reaction of aldehyde 62 and ethyl ketone 57. The development of a method for the construction of the AB spiroketal fragment is described and included the desymmetrization of C2-symmetric diketone 10 and the differentiation of the two primary alcohols of 16. Further elaboration of this advanced intermediate to the desired aldehyde 62 included an Evans' syn-aldol reaction and Tebbe olefination. The synthesis of the CD spiroketal fragment 56 involved the ketalization of a triol-dione, generated in situ by deprotection of 45, to provide a favorable ratio (6-7:1) of spiroketal isomers 46 and 47, respectively. The overall protecting group strategy, involving many selective manipulations of silyl protecting groups, was successfully developed to provide the desired C1-C28 subunit of spongistatin 1 (altohyrtin A) (65).

Studies in marine macrolide synthesis: Stereocontrolled synthesis of the AB-spiroacetal subunit of spongistatin 1 (altohyrtin A)

The C1-C13 subunit 2, containing the AB-spiroacetal ring system of spongistatin 1 (1), was prepared in 11 steps with 90% ds from 3-benzyloxypropanal. Key steps include (i) the aldol reaction between 4 and 11 using (-)-Ipc2