68985-11-5

Upstream product

• 31207-65-5 8α-acetoxy-13,14,15,16-tetranor-12-labdanoic acid 
• 103476-92-2 (3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan-2-ol 
• 97974-42-0 1-ethynyl-2,5,5,8a-tetramethyl-perhydro-4aH-1-naphthalenol 
• 1224876-02-1 2-[(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalen-1-yl]acetonitrile 
• 564-20-5 (3aR)-(+)-sclareolide 
• 190264-38-1 2-((1R,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl)-N-methoxy-N-methylacetamide 
• 61047-04-9 2-((1S,6S)-1,3,7,7-tetramethylbicyclo[4.4.0]dec-2-en-2-yl)ethyl acetate 
• 31222-15-8 2-[(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalen-1-yl]ethanol 
• 64061-39-8 (1R,2R,4aS,8aS)-(+)-1-(2'-acetoxyethyl)-1,2,3,4,4a,5,6,7,8,8a-decahydro-2-hydroxy-2,5,5,8a-tetramethylnaphthalene 

Downstream Products

• 6790-58-5 (-)-ambroxide 
• 564-20-5 (3aR)-(+)-sclareolide 

Relevant academic research and scientific papers

Synthesis of (+)-coronarin E

The labdane-type diterpenoid (+)-coronatin E (5) has been synthesized in 7 steps from (-)-sclareol (1) for the first time.

Synthesis from norambreinolide, structure, and antimicrobial activity of dihomodrimane sesquiterpenoids with azine, hydrazide, and dihydrazide fragments

12,12'-Azino-di-8α-hydroxy-11-dihomodrimane, N,N’-di-(8α-hydroxy-11-dihomodrim-12-ylidene)-adipic acid dihydrazide, N,N’-di-(Δ8,13-bicyclohomofarnesenoyl)-hydrazine, and hydrazides of Δ8,9- and Δ8,13-bicyclohomofarnesenoic

Lewis Acid-Catalyzed Stereoselective α-Addition of Chiral Aldehydes to Cyclic Dienol Silanes: Aqueous Synthesis of Chiral Butenolides

The stereoselective α-addition to cyclic dienol silanes has rarely been exploited, in contrast to the well-studied γ-addition of conjugated butenolides. In this study, an unprecedent catalytic Mukaiyama aldol α-addition of 2-trimetylsiloxy furan to optically pure aldehydes in water-containing solvents is reported. The synthetic utility of this concept was demonstrated in the efficient synthesis of six bioactive natural products: vitexolide D, curcucomosin C, villosin, chinensine C, (+)-coronarin E and (E)-labda-7,11,13-trien-16,15-olid.

Enantioselective access to (-)-Ambrox starting from β-farnesene

Starting from inexpensive (E)-β-farnesene (1), an eight-step enantioselective synthesis of the olfactively precious Ambrox ((-)-2a) has been performed. The crucial step is the catalytic asymmetric isomerization of (2E,6E)-N,N-diethylfarnesylamine (3) to t

Bioactive compounds with added value prepared from terpenes contained in solid wastes from the olive oil industry

Starting from solid wastes from two-phase olive-oil extraction, the pentacyclic triterpenes oleanolic acid and maslinic acid were isolated. These natural compounds were transformed into methyl olean-12-en-28-oate (5), which then was transformed into several seco-C-ring triterpene compounds by chemical and photolytic modifications. The triene seco-products were fragmented through several oxidative procedures to produce, simultaneously, cis- and trans-decalin derivatives, both potential synthons for bioactive compounds. The chemical behavior of the isolated fragments was investigated, and a suitable approach to several low-molecular-weight terpenes was performed. These are interesting processes for the value-addition to solid waste from the olive-oil industry.

PROCESS FOR THE PREPARATION OF TETRANORLABDANE DERIVATIVES

The present invention concerns a process for the preparation of a compound of formula (I), wherein the dotted line is a single bond and n is 1 or the dotted line is a double bond and n is 0, and wherein the relative configuration is as shown, in the form of any one of its diastereoisomers or enantiomers or mixtures thereof.

PROCESS FOR THE PREPARATION OF TETRANORLABDANE DERIVATIVES

The present invention concerns a process for the preparation of a compound of formula (I) wherein the dotted line is a single bond and n is 1 or the dotted line is a double bond and n is 0, and wherein the relative configuration is as shown, in the form of any one of its diastereoisomers or enantiomers or mixtures thereof.

Spiroperoxy lactones from furans in one pot: Synthesis of (+)-premnalane A

A [4+2]-cycloaddition between singlet oxygen and a furan, followed by an ene reaction and ketalization, in one synthetic operation, was used for the synthesis of (+)-premnalane A. The first example of a singlet oxygen ene reaction that furnishes exclusively a Z-double bond is noted.