97190-30-2

Upstream product

• 109-06-8 α-picoline 
• 119650-29-2 1-[(3aR,4R,5R,7aS)-5-((E)-4-Iodo-but-3-enyl)-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl]-ethanol 
• 123731-42-0 2-(2-pyridyl)ethyltriphenylphosphonium iodide 
• 123731-47-5 3-((3aR,4R,5R,7aS)-4-Acetyl-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl)-propionaldehyde 
• 123807-90-9 (3aS,5aR,10aR,10bR)-1,2,3,3a,5a,6,7,8,10a,10b-Decahydro-9-oxa-cyclohepta[e]inden-10-one 
• 120310-01-2 (2E,4E)-ethyl 7-(tert-butyldimethylsilyloxy)-hepta-2,4-dienoate 
• 120269-63-8 (2E,7E,9E)-12-(tert-Butyl-dimethyl-silanyloxy)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-dodeca-2,7,9-trien-1-one 
• 120269-66-1 Toluene-4-sulfonic acid 2-((3aR,4R,5R,7aS)-4-acetyl-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl)-ethyl ester 
• 109-04-6 2-bromo-pyridine 
• 123731-44-2 (R)-4-Benzyl-3-{(3aR,4R,5R,7aS)-5-[3-(4-methoxy-phenoxy)-propyl]-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carbonyl}-oxazolidin-2-one 
• 123731-43-1 (R)-4-Benzyl-3-[(2E,7E,9E)-13-(4-methoxy-phenoxy)-trideca-2,7,9-trienoyl]-oxazolidin-2-one 
• 123731-45-3 (R)-4-Benzyl-3-[(3aR,4R,5R,7aS)-5-(3-hydroxy-propyl)-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carbonyl]-oxazolidin-2-one 
• 123731-33-9 (2E,7E,9E)-13-(4-Methoxy-phenoxy)-trideca-2,7,9-trienoic acid methyl ester 
• 123731-31-7 2-[(4E,6E)-10-(4-Methoxy-phenoxy)-deca-4,6-dienyl]-[1,3]dioxolane 

Relevant academic research and scientific papers

Semipreparative synthesis, 13C-and 2D-NMR of Pulo'upone

A mmolar scale synthetic route to (±)-piuo'upone, in 9 steps, 3.8 % overall yield, and under non-epimerizing conditions, is reported. A complete assignment of the compound's 1H and 13C NMR shifts is presented.

ASYMMETRIC TOTAL SYNTHESES OF (+)- AND (-)-PULO'UPONE

Asymmetric total syntheses of both enantiomers of marine mollusk metabolite pulo'upone 1 have been achieved by Evans' asymmetric Diels-Alder reaction.

ENANTIOSELECTIVE SYNTHESIS AND ABSOLUTE CONFIGURATION OF (-)-PULO'UPONE BY ASYMMETRIC INTRAMOLECULAR DIELS-ALDER REACTION

(-)-Pulo'upone (1) was synthesized via an asymmetric, bornane-10,2-sultam- directed, intramolecular Diels-Alder reaction (3->2) and a 2-pyridylcuprate/allylacetate coupling (18->1).The (6'R,9'S,13'R,14'R)-configuration of (-)-1 follows from an X-ray diffraction analysis of the cycloaddition product 2.

TOTAL SYNTHESIS OF (+/-)-PULO'UPONE

The first total synthesis of the Hawaiian mollusk metabolite pulo'upone (2) has been achieved, wherein a novel retro hetero Diels-Alder/intramolecular Diels-Alder tandem process established the trans-fused hydrindene nucleus.