194294-70-7

Upstream product

• 194294-79-6 (R)-3-(4-Methoxy-benzyloxy)-hex-5-enoic acid methoxy-methyl-amide 
• 1035455-33-4 (3R)-3-[(4-methoxybenzyl)oxy]-5-hexen-1-ol 
• 1379678-59-7 C₁₈H₂₈O₄ 
• 175601-64-6 (R)-1,1-diethoxyhex-5-en-3-ol 
• 194294-69-4 (R)-3-Hydroxy-1-((R)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-hex-5-en-1-one 
• 194294-78-5 (R)-3-Hydroxy-hex-5-enoic acid methoxy-methyl-amide 
• 89238-99-3 O-(4-methoxybenzyl)-trichloroacetimidate 

Downstream Products

• 1035455-21-0 (R)-3-(4-methoxybenzyloxy)hex-5-enoic acid 
• 1190769-84-6 (3S,5R)-5-[(4-methoxybenzyl)oxy]-1-phenyl-7-octen-1-yn-3-ol 
• 1379678-65-5 C₂₀H₂₅NO₅ 
• 1379678-46-2 (2R,3S,5R)-2,3-carbonyldioxy-5-(4-methoxybenzylhydroxy)-(2-methoxyphenyl)oct-7-en-1-one 
• 1379678-45-1 (2R,3S,5R)-2,3-dihydroxy-5-(4-methoxybenzylhydroxy)(2-methoxyphenyl)oct-7-en-1-one 
• 1196801-02-1 C₅₂H₆₄O₈Si 
• 194294-71-8 (2R,4S,8S,10R)-4-(tert-Butyl-diphenyl-silanyloxy)-8-hydroxy-2,10-bis-(4-methoxy-benzyloxy)-1-(2-trimethylsilanyl-ethoxymethoxy)-tridec-12-en-6-one 

Relevant academic research and scientific papers

Total synthesis of laulimalide: Synthesis of the northern and southern fragments

The first stage in the development of a synthetic route for the total synthesis of laulimalide (1) is described. Our retrosynthetic analysis envisioned a novel macrocyclization route to the natural product by using a Ru-catalyzed alkene-alkyne coupling. This would be preceded by an esterification of the C19 hydroxyl group, joining together two equally sized synthons, the northern fragment 7 and the southern fragment 8. Our first generation approach to the northern fragment entailed a key sequential Ru/Pd coupling sequence to assemble the dihydropyran. The key reactions proceeded smoothly, but the inability to achieve a key olefin migration led to the development of an alternative route based on an asymmetric dinuclear Zn-catalyzed aldol reaction of a hydroxyl acylpyrrole. This key reaction led to the desired diol adduct 66 with excellent syn/anti selectivity (10:1), and allowed for the successful completion of the northern fragment 7. The key step for the synthesis of the southern fragment was a chemoselective Rh-catalyzed cycloisomerization reaction to form the dihydropyran ring from a diyne precursor. This reaction proved to be selective for the formation of a six-membered ring, over a seven. The use of an electron-deficient bidentate phosphine allowed for the reaction to proceed with a reduced catalyst loading. Making the pieces: The synthesis of two equal-sized fragments of laulimalide is described (see scheme). A key Rh-catalyzed cycloisomerization reaction allowed for an efficient synthesis of the endocyclic dihydropyran and a stereoselective acylpyrrole Zn-aldol reaction allowed for the formation of the syn-diol. Copyright

A concise stereoselective formal total synthesis of the cytotoxic macrolide (+)-Neopeltolide via Prins cyclization

A convergent and highly stereoselective formal total synthesis of the naturally occurring, cytotoxic 14-membered macrolide neopeltolide has been achieved via two Prins cyclizations.

A short stereoselective synthesis of (+)-(6R, 2′S)-cryptocaryalactone via ring-closing metathesis

A short stereoselective synthesis of (+)-(6R, 2′S)-cryptocaryalactone was successfully completed. Key steps included the application of Carreira's asymmetric alkynylation reaction to form a propargylic alcohol and subsequently lactone formation using the

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.

Total synthesis of (+)-neopeltolide by a Prins macrocyclization

(Chemical Equation Presented) Rings within rings: The total synthesis of (+)-neopeltolide was accomplished by employing an intramolecular Prins macrocyclization of an aldehydic homoallylic alcohol intermediate (see scheme).

A modular approach to marine macrolide construction. 2. Concise stereocontrolled synthesis of the C17-C28 (CD) spiroacetal component

The CD spiroacetal ring system of altohyrtin A, which houses one-fifth of the stereogenic centers resident in the macrolide, has been synthesized through a combination of aldol condensations having different stereocontrol elements.