101143-85-5

Basic information

• Product Name: (4aS,6aS,8S,9R,11aS,11bS)-4,4,9,11b-tetramethyltetradecahydro-8,11a-methanocyclohepta[a]naphthalen-9-ol
• CAS NO: 101143-85-5
• Molecular Formula: C₂₀H₃₄O
• Molecular Weight: 290.4834
• Mol File: 101143-85-5.mol

Chemical Properties

• Boiling Point: 378.6°C at 760 mmHg
• Flash Point: 161.7°C
• Density: 1.02g/cm³
• Vapor Pressure: 2.76E-07mmHg at 25°C
• Refractive Index: 1.533
• CAS DataBase Reference: (4aS,6aS,8S,9R,11aS,11bS)-4,4,9,11b-tetramethyltetradecahydro-8,11a-methanocyclohepta[a]naphthalen-9-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (4aS,6aS,8S,9R,11aS,11bS)-4,4,9,11b-tetramethyltetradecahydro-8,11a-methanocyclohepta[a]naphthalen-9-ol(101143-85-5)
• EPA Substance Registry System: (4aS,6aS,8S,9R,11aS,11bS)-4,4,9,11b-tetramethyltetradecahydro-8,11a-methanocyclohepta[a]naphthalen-9-ol(101143-85-5)

Safety Data

• Hazardous Substances Data: 101143-85-5(Hazardous Substances Data)

Upstream product

• 52592-12-8 17,18-diacetoxyaphidicol-3α,16β-diol 
• 38966-21-1 Aphidicolin 
• 74500-98-4 C₂₈H₄₀O₅S 
• 74501-02-3 C₂₃H₃₄O₅ 
• 74501-01-2 C₂₄H₃₆O₄ 
• 74501-05-6 C₂₃H₃₆O₃S₂ 
• 74501-03-4 C₂₃H₃₆O₅ 
• 74501-04-5 C₂₁H₃₂O₄ 
• 74500-99-5 (3aS,5aR,6R,9aS,9bR,11aS)-6,9a-Dimethyl-11-methylene-1-oxo-tetradecahydro-cyclobuta[d]phenanthrene-6-carboxylic acid methyl ester 
• 74501-00-1 (3aS,5aR,6R,9aS,9bR,11aS)-2,6,9a-Trimethyl-11-methylene-1-oxo-tetradecahydro-cyclobuta[d]phenanthrene-6-carboxylic acid methyl ester 
• 2651-32-3 (1R,4aS,8aS,10aR)-1,4a-Dimethyl-6-oxo-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydro-phenanthrene-1-carboxylic acid methyl ester 
• 74501-06-7 C₂₁H₃₄O₃ 
• 81672-02-8 C₂₁H₃₂O₂ 
• 60148-89-2 C₂₀H₃₂O 

Downstream Products

• 52592-29-7 aphidicol-16-en 
• 52645-90-6 aphidicol-15-ene 

Relevant articles and documents

Biosynthesis of diterpenoid aphidicolin: Isolation of intermediates from P-450 inhibitor treated mycelia of Phoma betae

Treatment of Phoma betae with P-450 inhibitors caused accumulation of biosynthetic precursors 2, 3 and 4 of aphidicolin (1). Their structures were elucidated by spectroscopic analysis and they were confirmed by chemical transformations from 1. Isotopicall

Construction of the stemodane nucleus by a hydroxyl-directed intramolecular ene reaction. Total synthesis of (±)-2-desoxystemodinone

A synthesis of the diterpene 2-desoxystemodinone was completed from the known tricyclic ketone 9 in eight steps and 35% overall yield. The key step involved a thermal intramolecular ene reaction of α-hydroxy aldehyde 21 which led to 24 in 94% yield. By contrast, a Lewis acid-catalyzed ene reaction of 21 gave oxetane 25 as the major product. The pivotal role of the hydroxyl substituent of 21 in facilitating the ene reaction was demonstrated and is rationalized by a hydrogen bond which orients the carbonyl in a favorable conformation for rearrangement.

Studies in Terpenoid Biosynthesis. Part 32. The Incorporation of Aphidicol-16-ene and Aphidicolan-16β-ol into the Diterpenoid Aphidicolin by the Fungus Cephalosporium aphidicola

The preparation of aphidicol-16-ene and aphidicolan-16β-ol and their incorporation into aphidicolin by Cephalosporium aphidicola to the extent of 0.09 and 7.9percent respectively, is described.

Biogenetic-Type Total Synthesis of (+/-)-2-Deoxystemodinone

A biogenetic-type total sythesis of (+/-)-2-deoxystemodinone (1), by solvolytic rearrangement of the 1-methylbicyclooct-2-yl methanesulfonate 4, is described.

Total synthesis of the stemodane-type diterpenoids, (+/-)-2-desoxystemodinone, (+)-2-desoxystemodinone, and (+/-)-stemodinol

Stereospecific total syntheses of (+/-)-2-desoxystemodinone, (+)-2-desoxystemodinone, and (+/-)-stemodinol are described.Also described are the isolation of (+)-2-desoxystemodinone from S. maritima and its characterization.A strategy for the elaboration o

Total synthesis of racemic 2-desoxystemodinone and stemodinol; the identity of natural "stemodinol" with stemarin

Total synthesis of the naturally occuring diterpinoid 2-desoxystemodinone (3) and the diterpenoid structure 2 ("stemodinol") are described.The synthetic diterpenoid 2 was not identical to an authentic sample of "stemodinol".The authentic sample was found to be stemarin to which structure 2 had been erroneously assigned in the literature.It would appear that the diterpenoid represented by 2 has not been isolated from natural sources.