76015-58-2

Basic information

• Product Name: (4aS)-4aα,5,5aα,6,6aα,6b-Hexahydro-3-(hydroxymethyl)-5-methylene-6bβ-methylcyclopropa[2,3]indeno[5,6-b]furan-2(4H)-one
• Synonyms: (4aS)-4aα,5,5aα,6,6aα,6b-Hexahydro-3-(hydroxymethyl)-5-methylene-6bβ-methylcyclopropa[2,3]indeno[5,6-b]furan-2(4H)-one;4aα,5,5aα,6,6aα,6b-Hexahydro-3-(hydroxymethyl)-6bβ-methyl-5-methylenecycloprop[2,3]indeno[5,6-b]furan-2(4H)-one;Onoseriolide
• CAS NO: 76015-58-2
• Molecular Formula: C15H16O3
• Molecular Weight: 244.28574
• Mol File: 76015-58-2.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (4aS)-4aα,5,5aα,6,6aα,6b-Hexahydro-3-(hydroxymethyl)-5-methylene-6bβ-methylcyclopropa[2,3]indeno[5,6-b]furan-2(4H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (4aS)-4aα,5,5aα,6,6aα,6b-Hexahydro-3-(hydroxymethyl)-5-methylene-6bβ-methylcyclopropa[2,3]indeno[5,6-b]furan-2(4H)-one(76015-58-2)
• EPA Substance Registry System: (4aS)-4aα,5,5aα,6,6aα,6b-Hexahydro-3-(hydroxymethyl)-5-methylene-6bβ-methylcyclopropa[2,3]indeno[5,6-b]furan-2(4H)-one(76015-58-2)

Safety Data

• Hazardous Substances Data: 76015-58-2(Hazardous Substances Data)

Usage

General Description

The chemical, also known as (-)-Podophyllotoxin, is a natural compound found in plants such as Podophyllum and Linum species. It is a potent cytotoxic and anti-tumor agent, and has been used in the development of cancer chemotherapy drugs. Its unique structure, consisting of a cyclopropa[2,3]indeno[5,6-b]furan-2(4H)-one framework, allows it to bind to and inhibit enzymes involved in cell division, making it useful in the treatment of various types of cancer. Additionally, (-)-Podophyllotoxin has also been investigated for its potential antiviral and antifungal properties.

Upstream product

• 487-51-4 4-carbethoxy-3-methyl-2-cyclohexen-1-one 
• 80-57-9 (-)-Verbenone 
• 74842-03-8 (±)-ethyl (7S,8R)-7-methyl-7-vinyl-1,4-dioxaspiro[4.5]decane-8-carboxylate 
• 74842-02-7 (±)-ethyl (1R,2S)-2-methyl-4-oxo-2-vinylcyclohexane-1-carboxylate 
• 128261-61-0 (4S,5S)-1-acetoxy-4-isopropenyl-5-methyl-5-vinyl-1-cyclohexene 
• 128261-62-1 (1R,4S,5R)-(+)-4,6,6-trimethyl-4-vinylbicyclo<3.1.1>heptan-2-one 
• 18309-32-5 Verbenone 
• 73215-93-7 bolivianine 

Relevant articles and documents

Asymmetric total synthesis of onoseriolide, bolivianine, and isobolivianine

In this article, we describe our efforts on the total synthesis of bolivianine (1) and isobolivianine (2), involving the synthesis of onoseriolide (3). The first generation synthesis of bolivianine was completed in 21 steps by following a chiral resolution strategy. Based on the potential biogenetic relationship between bolivianine (1), onoseriolide (3), and β-(E)-ocimene (8), the second generation synthesis of bolivianine was biomimetically achieved from commercially available (+)-verbenone in 14 steps. The improved total synthesis features an unprecedented palladium-catalyzed intramolecular cyclopropanation through an allylic metal carbene, for the construction of the ABC tricyclic system, and a Diels-Alder/intramolecular hetero-Diels-Alder (DA/IMHDA) cascade for installation of the EFG tricyclic skeleton with the correct stereochemistry. Transformation from bolivianine to isobolivianine was facilitated in the presence of acid. The biosynthetic mechanism and the excellent regio- and endo selectivities in the cascade are well supported by theoretical chemistry based on the DFT calculations. From terpenes to terpenes: Two strategies toward the synthesis of bolivianine are described. Based on the modified biogenetic hypothesis, biomimetic total synthesis was evolved and accomplished, involving onoseriolide, bolivianine, and isobolivianine (see figure). Experimental results and DFT calculations support a Diels-Alder/intramolecular hetero-Diels-Alder (DA/IMHDA) cascade leading to bolivianine. In addition, the synthesis features a new Pd-catalyzed intramolecular cyclopropanation. Copyright