1263-58-7

Upstream product

• 16625-53-9 2,3-seco-2,3-dihydroreserpine 
• 4521-61-3 3,4,5-Trimethoxybenzoyl chloride 
• 96648-90-7 (4aR^*,5S^*)-2-benzyl-5-((methoxymethoxy)methyl)-3,4,4a,5-tetrahydro-1(2H)-isoquinolone 
• 109961-00-4 (4aR^*,5S^*,6S^*,7S^*,8aS^*)-2-benzyl-7-((2'-ethylhexanoyl)oxy)-5-hydroxymethyl-6-methoxy-3,4,4a,5,6,7,8,8a-octahydro-1(2H)-isoquinolone 
• 70617-03-7 (4aR^*,5S^*,6S^*,7S^*,8aR^*)-6-methoxy-5-(methoxycarbonyl)-7-((3,4,5-trimethoxybenzoyl)oxy)perhydroisoquinoline 
• 109961-17-3 (4aR^*,5S^*,6S^*,7S^*,8aS^*)-2-benzyl-7-((2'-ethylhexanoyl)oxy)-6-methoxy-5-(methoxycarbonyl)perhydroisoquinoline 
• 96648-95-2 (4aR^*,5S^*,6S^*,7S^*,8aS^*)-2-benzyl-7-((2'-ethylhexanoyl)oxy)-6-methoxy-5-(methoxycarbonyl)-3,4,4a,5,6,7,8,8a-octahydro-1(2H)-isoquinolone 
• 109961-01-5 (4aR^*,5S^*,6S^*,7S^*,8aS^*)-2-benzyl-5-carboxyl-7-((2'-ethylhexanoyl)oxy)-6-methoxy-3,4,4a,5,6,7,8,8a-octahydro-1(2H)-isoquinolone 
• 96648-94-1 (4aR^*,5S^*,6S^*,7S^*,8aS^*)-2-benzyl-7-((2'-ethylhexanoyl)oxy)-6-methoxy-5-((methoxymethoxy)methyl)-3,4,4a,5,6,7,8,8a-octahydro-1(2H)-isoquinolone 
• 96648-93-0 (4aR^*,5S^*,6S^*,7S^*)-2-benzyl-7-((2'-ethylhexanoyl)oxy)-3,4,4a,5,6,7-hexahydro-6-methoxy-5-((methoxymethoxy)methyl)-1(2H)-isoquinolone 
• 96648-96-3 (4aR^*,5S^*,6S^*,7S^*,8aR^*)-2-benzyl-6-methoxy-5-(methoxycarbonyl)-7-((3,4,5-trimethoxybenzoyl)oxy)perhydroisoquinoline 
• 2901-66-8 (+/-)-methyl reserpate 
• 109961-18-4 (4aR^*,5S^*,6S^*,7S^*,8aR^*)-2-benzyl-7-hydroxy-6-methoxy-5-(methoxycarbonyl)perhydroisoquinoline 
• 109961-06-0 (4aR,5S,6R,7R)-2-Benzyl-7-(2-ethyl-hexanoyloxy)-6-methoxy-1-oxo-1,2,3,4,4a,5,6,7-octahydro-isoquinoline-5-carboxylic acid 

Relevant academic research and scientific papers

A Desymmetrization-Based Total Synthesis of Reserpine

Reported herein is a desymmetrization-based synthetic approach to the fused polycyclic indole alkaloid reserpine. The centerpiece of the developed strategy features an internal desymmetrization process that enabled the use of a readily accessible and nonstereogenic reserpine E-ring precursor, in contrast to the synthesis-intensive and stereodefined E-ring intermediates employed in all past reserpine syntheses. Utilization of inexpensive reagents through an orchestrated sequence of carefully selected chemical transformations further highlight the overall effectiveness of the developed pathway.

Regiospecific and stereoselective syntheses of (±)-reserpine and (-)-reserpine

Full details of three approaches to an entirely regio- and Stereoselective synthesis of the well-known target reserpine are described, culminating in a total synthesis which efficiently meets these requirements.

Genaral Strategies for the Synthesis of Indole Alkaloids. Total Syntheses of (+/-)-Reserpine and (+/-)-α-Yohimbine

The concise, total syntheses of the indole alkaloids (+/-)-reserpine (1) and (+/-)-α-yohimbine (4) have been completed by the application of a general strategy that features an intramolecular Diels-Alder reaction for the facile construction of the functio