99095-30-4

Upstream product

• 115463-10-0 ethyl (E)-7-(benzyloxy)hept-2-enoate 
• 100-39-0 benzyl bromide 
• 99016-97-4 (E)-7-(benzyloxy)-2-hepten-1-ol 
• 871732-99-9 7-benzyloxy-hept-2-enoic acid ethyl ester 
• 4541-15-5 5-(benzyloxy)-1-pentanol 
• 111-29-5 1 ,5-pentanediol 
• 78999-24-3 5-benzyloxy-1-pentanal 

Downstream Products

• 1187935-00-7 (2R,3S)-2-[4-(benzyloxy)butyl]-3-(iodo-methyl)oxirane 
• 910330-79-9 (R)-4-(4-Benzyloxy-butyl)-2,2-dimethyl-[1,3]dioxane 
• 1028432-69-0 C₂₂H₃₀O₅ 

Relevant academic research and scientific papers

Bisnucleophilic substitution as a synthetic tool for ready access to the piperidine alkaloids (+)-Connine, (+)-β-conhydrine, (+)-8-ethylnorlobelol, and (-)-halosaline

Herein we report the stereoselective total synthesis of (+)-connine, (+)-β-conhydrine, (+)-8-ethylnorlobelol, and (-)-halosaline via bisnucleophilic substitution with benzylamine as the key step.

Assembly of the southern macrocyclic half of (+)-spirastrellolide a through cyclic acetal tethered ring-closing metathesis and 1,3-anti-mukaiyama-aldol

We describe herein details of our efforts in syntheses of A-ring and BC-ring of (+)-spirastrellolide A. While the former would constitute a facile 12-step synthetic endeavor starting from 1,5-pentanediol, the latter would showcase a cyclic acetal-tethered

Stereoselective total synthesis of polyketide lactone, (3R,4S,5S,9S)-3,5,9-trihydroxy-4-methylundecanoic acid δ-lactone

The total synthesis of lactone 1 has been described. The convergent asymmetric synthesis relies on the use of an Evans' syn-aldol, chain extension with lithio tert-butyl acetate, and the stereoselective reduction of a ketone as the key reactions.

Synthesis of the C1-C16 fragment of spirastrellolide A

Synthesis of the C1-C16 fragment of spirastrellolide A is described here featuring Sharpless asymmetric epoxidation, an acid promoted O-1,4-addition, and Mukaiyama 1,3-anti-aldol.