140923-35-9

Basic information

• Product Name: 6-Hydroxy-5,6-dehydrosugiol
• Synonyms: 6-Hydroxy-5,6-dehydrosugiol;Montbretrol
• CAS NO: 140923-35-9
• Molecular Formula: C20H26O3
• Molecular Weight: 314.41864
• Mol File: 140923-35-9.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-Hydroxy-5,6-dehydrosugiol(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Hydroxy-5,6-dehydrosugiol(140923-35-9)
• EPA Substance Registry System: 6-Hydroxy-5,6-dehydrosugiol(140923-35-9)

Safety Data

• Hazardous Substances Data: 140923-35-9(Hazardous Substances Data)

Upstream product

• 901-41-7 (+/-)-sugiol methyl ether 
• 10064-26-3 (+/-)-ferruginyl methyl ether 
• 94608-98-7 (+/-)-6-hydroxy-5,6-dehydrosugiyl methyl ether 
• 70614-86-7 (4aS,10aS)-7-isopropyl-6-methoxy-1,1,4a-trimethyl-1,2,3,4,4a,10a-hexahydrophenanthrene 
• 269719-14-4 (4aS,10aS)-7-Isopropyl-6-methoxy-1,1,4a-trimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-ol 
• 901-41-7 sugiol methylether 
• 64199-80-0 O-methyl ferruginol 
• 514-62-5 ferruginol 
• 15340-79-1 ferruginol acetate 
• 19407-28-4 ar-abietatriene 
• 79593-19-4 (+)-(4aS,10aS)-6-acetyl-7-isopropyl-1,1,4a-trimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene 
• 1243263-22-0 (4aR)-6-(acetyloxy)-10-hydroxy-7-isopropyl-1,1,4a-trimethyl-2,3,4,4a-tetrahydro-9(1H)-phenanthrenone 

Relevant articles and documents

Connecting C19 norditerpenoids to C20 diterpenes: Total syntheses of 6-Hydroxy-5,6-dehydrosugiol, 6-Hydroxysugiol, and taiwaniaquinone H, and formal synthesis of dichroanone

Oxidation of the B-ring of abietane derivatives by Sharpless dihydroxylation gave the natural products 6-hydroxy-5,6-dehydrosugiol and 6-hydroxysugiol. Moreover, further oxidation gave a hydroxy dione derivative that provides a synthetic entry into the Ctaiwaniaquinoid family of natural products. This route is based on biosynthetic considerations and involves a benzilic acid rearrangement followed by decarboxylation. On the basis of this approach, a total synthesis of (-)-taiwaniaquinone H and a formal synthesis of (-)-dichroanone have been achieved. Georg Thieme Verlag Stuttgart - New York.

Synthesis of C-7 oxidized abietane diterpenes from racemic ferruginyl methyl ether

A series of naturally occurring C-7 oxidized abietane diterpenes have been synthesized from racemic ferruginyl methyl ether in high yields. 6-Hydroxyl-5,6-dehydrosugiol (7) can be converted into stable xanthoperol (12) using high temperature. Among the products, the structures of sugiyl methyl ether (2) and 6(-hydroxysugiyl methyl ether (8) were determined by X-ray analysis.