192566-65-7

Usage

Uses

Used in Medicinal Chemistry:
(5S,6S)-5-hydroxy-4,5-di(hydroxymethyl)-6,10,10-trimethylbicyclo[4.4.0]dec-3-en-2-one is used as a potential candidate in medicinal chemistry for its unique structure and functional groups. (5S,6S)-5-hydroxy-4,5-di(hydroxymethyl)-6,10,10-trimethylbicyclo[4.4.0]dec-3-en-2-one's reactivity and potential biological activity make it a promising molecule for the development of new pharmaceuticals.
Used as a Synthetic Intermediate in Organic Synthesis:
(5S,6S)-5-hydroxy-4,5-di(hydroxymethyl)-6,10,10-trimethylbicyclo[4.4.0]dec-3-en-2-one is used as a synthetic intermediate in organic synthesis due to its complex structure and the possibility of molecular manipulation. This allows for the creation of new compounds and the exploration of novel chemical reactions.

Upstream product

• 192566-60-2 12-acetoxy-9α,11-carbonyldioxydrim-7-en-6-one 
• 127681-58-7 (4R,4aS,8aS)-4-Hydroxy-4-(hydroxymethyl)-3,4a,8,8-tetramethyl-4a,5,6,7,8,8a-hexahydronaphthalen-1(4H)-one 
• 127681-57-6 (4aS,8aS)-3,4a,8,8-Tetramethyl-4-methylene-4a,5,6,7,8,8a-hexahydronaphthalen-1(4H)-one 
• 158426-26-7 12-acetoxy-9α,11-carbonyldioxydrim-7-ene 

Relevant academic research and scientific papers

Chemistry of zamoranic acid. Part 10. Homochiral hemisynthesis of pereniporin A

The synthetic versatility of 12-acetoxydrima-7,9(11)-diene 1 obtained from 15-hydroxylabda-7,13-dien-17-oic acid (zamoranic acid), as a key intermediate in the homochiral semisynthesis of highly functionalized drimanes such as pereniporin A 3, an important antibiotic, through the carbonate 2, is highlighted.

Formal synthesis of (-)-pereniporin B and (-)-cinnamosmolide

The paper describes a new pathway for an efficient synthesis of natural and bioactive drimanic compounds (-)-pereniporin B (1) and (-)-cinnamosmolide (2) from ketodiol 7, an intermediate obtained before from accessible labdane diterpenoid (+)-larixol (3). The key step involves allylic bromination of acetate 8 with N-bromosuccinimide. The in vitro antimicrobial and antifungal activities of all compounds are also reported. Their structures were confirmed by both spectroscopic data and chemical transformations.