Asperdiol

Base Information

• Chemical Name: Asperdiol
• CAS No.: 64180-67-2
• Molecular Formula: C₂₀H₃₂O₃
• Molecular Weight: 320.472
• NSC Number: 279559
• DSSTox Substance ID: DTXSID00418489
• ChEMBL ID: CHEMBL1989490
• Mol file: 64180-67-2.mol

Synonyms:ASPERDIOL;64180-67-2;NSC279559;CHEMBL1989490;DTXSID00418489;15-Oxabicyclo[12.1.0]pentadeca-4,10-diene-4-methanol, 6-hydroxy-10,14-dimethyl-7-(1-methylethenyl)-, [1R-(1R*,4E,6S*,7R*,10E,14R*)]-;NSC-279559

Chemical Property of Asperdiol

Chemical Property:

• Vapor Pressure: 8.62E-10mmHg at 25°C
• Boiling Point: 445°Cat760mmHg
• PKA: 14.10±0.70(Predicted)
• Flash Point: 223°C
• PSA: 52.99000
• Density: 1.012g/cm³
• LogP: 3.91630
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 320.23514488
• Heavy Atom Count: 23
• Complexity: 491

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCCC2(C(O2)CCC(=CC(C(CC1)C(=C)C)O)CO)C
• Isomeric SMILES: C/C/1=C\CCC2(C(O2)CC/C(=C\C(C(CC1)C(=C)C)O)/CO)C
• General Description: (1R,4E,6S,7R,10E,14R)-6-Hydroxy-10,14-dimethyl-7-(1-methylethenyl)-15-oxabicyclo[12.1.0]pentadeca-4,10-diene-4-methanol, also known as asperdiol or NSC 279559, is an anticancer cembrenoid characterized by a complex macrocyclic structure with a 15-oxabicyclo[12.1.0]pentadecane core. It features hydroxyl and isopropenyl substituents at specific positions, contributing to its bioactive properties. The compound's synthesis involves stereoselective epoxidation and rearrangement strategies, highlighting its structural complexity and potential therapeutic relevance.

Technology Process of Asperdiol

There total 26 articles about Asperdiol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 71.0%

[(4E,10E)-(1R,6S,7R,14R)-6-(2-Ethoxy-ethoxy)-7-isopropenyl-10,14-dimethyl-15-oxa-bicyclo[12.1.0]pentadeca-4,10-dien-4-yl]-methanol (104322-56-7) → asperdiol (64180-67-2)

Guidance literature:

With pyridinium p-toluenesulfonate; In tert-butyl alcohol; at 23 ℃; for 2.5h;

DOI:10.1021/ja00280a046

Reference yield: 62.6%

asperdiol acetate (198494-48-3) → asperdiol (64180-67-2) + (+)-(1R,2S,7R,11R,12R,3E)-7,11-oxacembra-3,8(19),15(17)-trien-2,12,18-triol

Guidance literature:

In isopropyl alcohol; at 25 ℃; for 12h; Irradiation;

DOI:10.1016/j.bmc.2012.10.022

Reference yield: 51.0%

(4E,10E)-(1S,6R,7S,14S)-4-Benzyloxymethoxymethyl-7-isopropenyl-10,14-dimethyl-15-oxa-bicyclo[12.1.0]pentadeca-4,10-dien-6-ol (87829-33-2,87861-06-1) → (+/-)-asperdiol (64180-67-2,86853-19-2,107171-99-3)

Guidance literature:

With ammonia; sodium; at -78 ℃; for 0.0166667h;

DOI:10.1021/jo00172a070

upstream raw materials:

[(4E,10E)-(1R,6S,7R,14R)-6-(2-Ethoxy-ethoxy)-7-isopropenyl-10,14-dimethyl-15-oxa-bicyclo[12.1.0]pentadeca-4,10-dien-4-yl]-methanol

(4E,10E)-(1R,6S,7R,14R)-6-(2-Ethoxy-ethoxy)-7-isopropenyl-10,14-dimethyl-15-oxa-bicyclo[12.1.0]pentadeca-4,10-diene-4-carboxylic acid ethyl ester

tert-Butyl-{(E)-(2R,3R)-2-(2-ethoxy-ethoxy)-9-[(2R,3R)-3-(2-iodo-ethyl)-2-methyl-oxiranyl]-3-isopropenyl-6-methyl-non-6-enyloxy}-dimethyl-silane

Methanesulfonic acid 2-((2R,3R)-3-{(E)-(R)-7-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(2-ethoxy-ethoxy)-ethyl]-4,8-dimethyl-nona-3,8-dienyl}-3-methyl-oxiranyl)-ethyl ester

Refernces

Cyclization of Polyenes. 46. Synthesis of (+/-)-Asperdiol, an Anticancer Cembrenoid

10.1021/jo00385a028

The study focuses on the synthesis of asperdiol, an anticancer cembrenoid, through a series of complex organic reactions. Key chemicals involved include cis- and trans-isopropenyl alcohols (3a and 3b) as starting materials, which are selectively functionalized to construct the asperdiol skeleton. The process involves selective epoxidation of double bonds, regioselective opening of epoxide rings using Sharpless conditions, and stereoselective rearrangements to achieve the desired macrocyclic structure. The study also explores the conformational properties of cembrenoid intermediates and their stability. The final stage involves the introduction of an epoxide ring to the C6-C7 double bond, leading to the successful synthesis of asperdiol and its geometrical isomer. The study demonstrates the importance of selective functionalization and rearrangement in the construction of complex natural products.