125131-19-3

Upstream product

• 51594-55-9 (R)-(-)-epichlorohydrin 
• 75-24-1 trimethylaluminum 
• 101906-25-6 (2R)-benzyl-(2-methylpent-4-ynyl) ether 
• 86951-92-0 (2S)-3-Benzyloxy-2-methyl-1-p-(toluenesulphonyloxy)propane 
• 63930-49-4 (R)-3-(benzyloxy)-2-methylpropan-1-ol 

Downstream Products

• 125131-20-6 (4E)-(2R,7R)-1-Benzyloxy-2,4-dimethyl-7,8-epoxy-4-octene 
• 130767-06-5 (2S,6S,8R,9S)-2-<(5R)-(2E)-6-Benzyloxy-3,5-dimethyl-2-hexen-1-yl>-8,9-dimethyl-1,7-dioxaspiro<5.5>undec-4-ene 
• 125131-21-7 (4E)-(2R,7R,9RS,14S,15R)-1-Benzyloxy-15-(tert-butyldimethylsiloxy)-11-methoxy-2,4,14-trimethyl-4,9,10-hexadecatrien-7-ol 
• 101906-32-5 (2R,4R,6R,8R,9S)-2-((E)-(R)-6-Benzyloxy-3,5-dimethyl-hex-2-enyl)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undecan-4-ol 
• 101906-32-5 (2S,4S,6S,8R,9S)-2-<(5R)-(2E)-6-Benzyloxy-3,5-dimethyl-2-hexen-1-yl>-8,9-dimethyl-4-hydroxy-1,7-dioxaspiro<5.5>undecane 
• 101906-21-2 [(2R,4R,6R,8R,9S)-2-((E)-(R)-6-Benzyloxy-3,5-dimethyl-hex-2-enyl)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-4-yloxy]-tert-butyl-dimethyl-silane 
• 130767-07-6 (E)-(2R,3S,10R,15R)-16-Benzyloxy-6-methoxy-3,13,15-trimethyl-hexadeca-6,7,12-triene-2,10-diol 
• 101906-21-2 (2R,4R,6S,8R,9S)-2-<(5R)-(2E)-6-benzyloxy-3,5-dimethyl-hex-2-en-1-yl>-8,9-dimethyl-4-(dimethyl-t-butylsilyloxy)-1,7-dioxaspiro<5.5>undecane 
• 130767-17-8 (7Z,12E)-(2R,3S,10S,15R)-16-Benzyloxy-2,10-dihydroxy-3,13,15-trimethyl-hexadeca-7,12-dien-6-one 
• 130767-17-8 (7E,12E)-(2R,3S,10S,15R)-16-Benzyloxy-2,10-dihydroxy-3,13,15-trimethyl-hexadeca-7,12-dien-6-one 

Relevant academic research and scientific papers

A NEW APPROACH TO 1,7-DIOXASPIROUNDEC-4-ENES VIA METALLATED ALLENOL ETHERS. SYNTHESIS OF LACRIMIN A.

Key steps in the first total synthesis of Lacrimin A (2) include (a) the use of methoxyallene as an enone-1,3-dianion equivalent; (b) the use of a new copper-catalysed migratory insertion reaction to construct a tri-substituted alkene stereoselectively; and (c) the use of a Pd(0)-catalysed coupling reaction to generate an isochromanone ring.

A SYNTHESIS OF LACRIMIN A

A convergent synthesis of Lacrimin A (2) is described in which a Wadsworth-Emmons reaction was used to constract the C10-C11 double bond and link the isochroman-1-one phosphonate (4) to the spiroacetal aldehyde (3).