264603-19-2

Upstream product

• 58931-16-1 (R)-1-benzyloxypent-4-en-2-ol 
• 89238-99-3 O-(4-methoxybenzyl)-trichloroacetimidate 
• 824-94-2 p-methoxybenzyl chloride 
• 14618-80-5 (R)-benzyl glycidol 
• 100-39-0 benzyl bromide 
• 2746-25-0 p-Methoxybenzyl bromide 

Downstream Products

• 264603-33-0 2-[(4R)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-pentyl]-6-methyl-pyran-4-one 
• 264603-34-1 (6R,8R,10R)-8-benzyloxymethyl-10-(tert-butyl-dimethyl-silanyloxy)-2-(2-hydroxy-butyl)-1,7-dioxa-spiro[5.5]undec-2-en-4-one 
• 264603-23-8 (6R,8R,10S)-8-benzyloxymethyl-10-(tert-butyl-dimethyl-silanyloxy)-2-(2-hydroxy-butyl)-1,7-dioxa-spiro[5.5]undec-2-en-4-one 
• 264603-22-7 2-[(4R)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-pentyl]-6-(2-hydroxy-butyl)-pyran-4-one 
• 264603-20-5 2-[(4R)-5-benzyloxy-2-hydroxy-4-(4-methoxy-benzyloxy)-pentyl]-6-methyl-pyran-4-one 
• 264603-21-6 2-[(4R)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-pentyl]-6-methyl-pyran-4-one 
• 264603-16-9 (3R)-4-benzyloxy-3-(4-methoxy-benzyloxy)-butyraldehyde 

Relevant academic research and scientific papers

Short diastereoselective synthesis of the C1-C13 (AB Spiroacetal) and C17-C28 fragments (CD spiroacetal) of spongistatin 1 and 2 through double chain-elongation reactions

A unique and practical synthetic sequence for rapid access to polyketides and to further the spiroacetals derived from them, which utilizes a bidirectional Hosomi-Sakurai allylation approach around key allylsilanes in the synthesis of the AB and CD ring s

Enantioselective synthesis of structurally intricate and complementary polyoxygenated building blocks of spongistatin 1 (altohyrtin a)

Enantioselective approaches to the construction of four complex building blocks of the structurally intricate marine macrolide known as spongistatin 1 are presented. The first phase of the synthetic effort relies on a practical approach to a desymmetrized, enantiomerically pure spiroketal ring system incorporating rings A and B. Concurrently, the C17-C28 subunit, which houses one-fifth of the stereogenic centers of the target in the form of rings C and D, was assembled via a composite of stereocontrolled aldol condensations. Once arrival at the entire C1-C28 sector had been realized, routes were devised to provide two additional highly functionalized sectors consisting of C29-C44 and C38-C51. A series of subsequent transformations including cyclization of the E ring and hydroboration to afford the B-alkyl intermediate for the key Suzuki coupling to append the side chain took advantage of efficient stereocontrol. Ultimately, complete assembly and functionalization of the western EF sector of spongistatin was thwarted by an inoperative Suzuki coupling step intended to join the side chain to the C29-C44 sector, and later because of complications due to protecting groups, which precluded the complete elaboration of the late stage C29-C51 intermediate.

Natural product-guided synthesis of a spiroacetal collection reveals modulators of tubulin cytoskeleton integrity

The spiro[5.5]ketal moiety forms the underlying structural skeleton of numerous biologically active natural products. Since simplified but characteristic spiroketals derived from the parent natural products retain biological activity, the spiro[5.5]ketal

Synthesis of the C16-C28 spiroketal Subunit of spongistatin 1 (altohyrtin A): The pyrone approach

(Equation presented) The synthesis of the CD spiroketal fragment of spongistatin 1 (altohyrtin A) has been accomplished utilizing the addition of a metalated pyrone to an aldehyde and subsequent acid-catalyzed spirocyclization. A stereoselective hydrogena