565228-87-7

Upstream product

• 101711-78-8 (3R)-3-propionyl-4-benzyloxazolidin-2-one 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 186885-60-9 [[3-(2R,3R)-4R]-3-(3-hydroxy-2,4-dimethyl-1-oxopent-4-enyl)-4-(phenylmethyl)]-2-oxazolidinone 

Downstream Products

• 1415730-34-5 (2S,4S,7S,8R,9S,10S,11R)-4-(tert-butyldimethylsilyloxy)-1-((4-methoxyphenyl)oxy)-7-hydroxy-2,8,10,12-tetramethyl-9,11-[(bis-dimethylmethylene)dioxy]-tridec-12-en-5-one 
• 1415730-28-7 (2S,4S,7R,8R,9S,10S,11R)-4-(tert-butyldimethylsilyloxy)-1-((4-methoxyphenyl)oxy)-7-hydroxy-2,8,10,12-tetramethyl-9,11-[(bis-dimethylmethylene)dioxy]-tridec-12-en-5-one 
• 1415730-29-8 (2S,4S,7R,8R,9S,10S,11R)-4,11-bis(tert-butyldimethylsilyloxy)-9-triethylsilyloxy-7-hydroxy-1-(4-methoxybenzyl)oxy-2,8,10,12-tetramethyltridec-12-en-5-one 
• 1415730-38-9 (2S,4S,7S,8R,9S,10S,11R)-4,11-bis(tert-butyldimethylsilyloxy)-9-triethylsilyloxy-7-hydroxy-1-(4-methoxybenzyl)oxy-2,8,10,12-tetramethyltridec-12-en-5-one 
• 1415730-41-4 (2S,4S,7R,8R,9S,10S,11R)-4,11-bis(tert-butyldimethylsilyloxy)-7,9-dihydroxy-1-(4-methoxybenzyl)oxy-2,8,10,12-tetramethyltridec-12-en-5-one 
• 1415730-42-5 (2R,4R,5R,6S)-2-[(1S,3S)-1-(tert-butyldimethylsilyloxy)-4-(4-methoxyphenyl)oxy-3-methylbutanyl]-6-[(1S,2R)-2-(tert-butyldimethylsilyloxy)-1,3-dimethylbut-3-enyl]-2,4-dihydroxy-5-methyltetrahydro-2H-pyran 
• 870773-92-5 (2S,3S,6R,7R,8S,9S,10S)-1,9,11-Tris-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-7-(4-methoxy-benzyloxy)-2,6,8,10-tetramethyl-undecan-5-one 
• 870773-87-8 (3R,4R,5S,6S,7S)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3,5,7-trimethyl-octan-2-one 
• 883292-60-2 (2S,4S,5S)-4-[(1S,2S,3S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-1,3-dimethyl-butyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane 

Relevant academic research and scientific papers

Simplified discodermolide analogues: Synthesis and biological evaluation of 4-epi-7-dehydroxy-14,16-didemethyl-(+)-discodermolides as microtubule-stabilizing agents

Several novel analogues of (+)-discodermolide were synthesized via a convergent strategy that used Wittig reactions to append left and right side chains to a central scaffold and then tested for biological activity. Three of the analogues in the 4-epi-7-d

A synthetic approach to the phorboxazoles – Synthesis of the C20–C32 central core

An enantiospecific synthesis of the C20–C32 central core of the phorboxazole scaffold, including the non-macrocyclic oxazole is detailed in 17 steps (longest linear sequence) from methacrolein in 7.8% overall yield. All of the stereocenters are communicated from a single Evans aldol reaction, and the final compound is suitably functionalized for further elaboration to the natural products.

Stereoselectivity of model C22-23 aldol coupling for spirangiens A & B

A model system was prepared to investigate the diastereoselectivity of the key C22-23 aldol coupling for the synthesis of spirangiens A & B. The lithium enolate of model ketone 3 was coupled with the differently protected aldehydes 4 (acetonide) and 5 (silyl) giving 3:1 and 3.5:1 dr, respectively, in favour of the unnatural (S) isomer in both cases. The lack of any significant effect on the aldol stereoselectivity induced by the aldehyde protecting groups contrasts with previous literature reports.

Studies on the total synthesis of sanglifehrin A: Stereoselective synthesis of the C(29)-C(39) fragment

A highly stereoselective synthesis of the C(29)-C(39) fragment of the potent immunosuppressant sanglifehrin A has been accomplished by a sequence involving 16 steps (18% overall yield) from N-propionyloxazolidinone 9. Key steps are a diastereoselective hy

ANALOGS OF DISCODERMOLIDE AND DICTYOSTATIN-1, INTERMEDIATES THEREFOR AND METHODS OF SYNTHESIS THEREOF

A compound of the following structure: wherein R1 is H, an alkyl group, an aryl group, an alkenyl group, an alkynyl group, or a halogen atom; R2 is H, an alkyl group, an aryl group, a benzyl group, a trityl group, -SiRaRbRc, CH2ORd, or CORe; Ra, Rb and Rc are independently an alkyl group or an aryl group; Rd is an alkyl group, an aryl group, an alkoxylalkyl group, -RiSiRaRbRc or a benzyl group, wherein Ri is an alkylene group; Re is an alkyl group, an allyl group, a benzyl group, an aryl group, an alkoxy group, or -NRgRh, wherein Rg and Rh are independently H, an alkyl group or an aryl group; R3 is (CH2)n where n is and integer in the range of 0 to 5, -CH2CH(CH3)-, -CH=CH-, -CH=C(CH3)-, or -C=-C-; R4 is (CH2)p where p is an integer in the range of 4 to 12, -(CHRkl)yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5C(Rsl )=C(Rs2)C(Rs3)=C(Rs4)-, -(CHRk1 )yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5CH(RsI)CH(Rs2)C(Rs3)=C(Rs4)-, -(CHRk1)yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRks)y5C(Rsl)=C(Rs2)CH(Rs3)CH(Rs4)-, -(CHRkI )yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5CH(Rsl)CH(Rs2)CH(Rs3)CH(R s4)-,wherein y1 and y2 are 1 and y3, y4 and y5 are independently 0 or 1, Rk1, Rk2, Rk3, Rk4 and Rk5 are independently H, CH3, or OR2a, and Rs1,Rs2, Rs3, and Rs4 are independently H or CH3, wherein R2a is H, an alkyl group, an aryl group, a benzyl group, a trityl group, -SiRaRbRc, CH2ORd, or CORe; and R5 is H or OR2b, wherein R2b is H, an alkyl group, an aryl group, an aryl group, a benzyl group, a trityl group, -SiRaRbRc, CH2ORd, or CORe; provided that the compound is not dictyostatin 1.