32981-89-8

Usage

Source

Derived from the Pacific yew tree (Taxus brevifolia)

Precursor

To the anticancer drug paclitaxel

Chemical structure

Highly complex diterpenoid compound with a pentacyclic core

Known for

Strong cytotoxic effects against cancer cells

Role

Important intermediate in the semi-synthesis of paclitaxel

Research focus

Development of more efficient and sustainable production methods

Uniqueness

Unique chemical structure and potent biological activity

Value

Valuable target for drug discovery and development in cancer treatment

Upstream product

• 27548-93-2 baccatin III 
• 150665-56-8 7-O-triethylsilyl-13-keto baccatin III 
• 71610-00-9 Cephalomannine 
• 155588-21-9 7-triethylsilyl-13-dehydro-10-deacetylbaccatin III 
• 115437-18-8 7-triethylsilyl-10-deacetylbaccatin III 
• 108-24-7 acetic anhydride 
• 92950-42-0 13-dehydro-10-deacetylbaccatin III 

Downstream Products

• 518021-32-4 C₃₆H₄₄O₁₃ 
• 518021-34-6 C₃₇H₄₂O₁₅ 
• 518021-33-5 C₃₆H₄₄O₁₄ 

Relevant academic research and scientific papers

Design, synthesis and structure-activity relationships of novel taxane-based multidrug resistance reversal agents

A series of novel taxane-based multidrug resistance (MDR) reversal agents (TRAs) has been designed and synthesized. Structure - activity relationship (SAR) study clearly indicates that modification of the C-7 position with hydrophobic arenecarbonylcinnamoyl groups brings about high potency against drug efflux mediated by P-glycoprotein (P-gp). Six TRAs exhibit ability to modulate a wide range of ATP-binding cassette (ABC) transporters, such as P-gp, multidrug resistance-associated protein 1 (MRP1), and breast cancer resistance protein (BCRP), which may serve as novel broad-spectrum modulators of ABC transporters.

Diastereoselective 14beta-hydroxylation of baccatin III derivatives.

14beta-Hydroxybaccatin III, a compound with limited availability by natural sources, is the starting material for the synthesis of the second-generation anticancer taxoid ortataxel. The 7-tert-butoxycarbonyl (1a) and 7-triethylsilyl (1b) derivatives of 14beta-hydroxybaccatin III 1,14-carbonate were synthesized from 10-deacetylbaccatin III (3). The crucial steps were (a) the C(14)beta hydroxylation of the corresponding 13-oxobaccatin III derivatives by oxaziridine-mediated electrophilic oxidation and (b) the reduction of the C(13) carbonyl group with sodium or alkylammonium borohydrides. This protocol provides a practical way for the semisynthesis of ortataxel from 10-deacetylbaccatin III, a compound readily available from various yews.

A mild and efficient approach for the deprotection of silyl ethers by sodium periodate

A mild and efficient method for the deprotection of silyl ethers is reported. The most often used silyl protecting groups, such as TBDMS, TIPS, TMS, TES, TIBS, TPS can be cleaved by NaIO4 furnishing the corresponding alcohol in high yields. This method can be used for a wide range of substrates.

The chemistry of the taxane diterpene: Stereoselective synthesis of 10-deacetoxy-11,12-expoxypaclitaxel

Epoxidation of the olefin in 10-deacetoxybaccatin III (6) and 10-deacetoxypaclitaxel (9) was accomplished with meta-chloroperbenzoic acid leading to a novel pentacyclic ring system. Hydroxyl directed delivery of the epoxidizing agent did not appear to pla

Anitleukemic Alkaloids from Taxus wallichiana Zucc.

A new antileukemic taxane alkaloid, cephalomannine (1a), has been isolated from leaves, stems, and roots of Taxus wallichiana Zucc.Cephalomannine is closely related to taxol (1b), a previously characterized antileukemic alkaloid, which also occurs in T. wallichiana but in lesser amounts than cephalomannine.The new alkaloid and its hydrolysis products were characterized by nuclear magnetic resonance, mass spetroscopy, and X-ray crystallography; taxol and two cytotoxic taxane congeners were also identified.