103476-92-2

Upstream product

• 138171-15-0 8-acetoxy-labdanolic acid 
• 564-20-5 (3aR)-(+)-sclareolide 
• 145511-17-7 15-nor-8-acetoxy-13-labdene 
• 469-11-4 labdanolic acid 
• 14162-41-5 (13R,14RS)-14,15-epoxylabdane-8,13-diol 
• 64661-55-8 (12R)-8α,12-epoxy-14,15-bisnorlabdan-13-one 
• 5153-92-4 sclareol oxide 
• 159970-19-1 8α,12-epoxy-13,14,15,16-tetranorlabdan-12-ol acetate 
• 145511-19-9 15-nor-8-hydroxy-12-labdene 

Downstream Products

• 913379-65-4 C₂₄H₃₄O₂ 
• 72853-86-2 (1R,2S)-1-(2,5-Dimethoxy-benzyl)-1,2,5,5-tetramethyl-1,2,3,4,5,6,7,8-octahydro-naphthalene 
• 20404-65-3 (-)-(2R,4aS,8aS)-2,5,5,8a-Tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1(2H)-one 
• 39707-54-5 (-)-ent-zonarol 
• 250146-75-9 ent-isozonarol 
• 39707-56-7 (+)-zonarone 
• 39707-59-0 ent-isozonarone 
• 752211-90-8 4-hydroxy-3-(((1R,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl)methyl)benzoic acid 
• 1376654-81-7 C₃₆H₄₄O₄ 
• 1376654-71-5 C₂₃H₃₄O₃ 
• 1376654-68-0 (1R,2R,4aS,8aS)-2,5,5,8a-tetramethyl-1-(4-(trifluoromethyl)benzyl) decahydronaphthalen-2-ol 
• 1376654-34-0 (+)-yahazunone 
• 849669-49-4 (1R,2R,4aS,8aS)-1-(5-ethyl-2,3-diMethoxybenzyl)-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol 
• 68985-11-5 [(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalen-1-yl]acetaldehyde 

Relevant academic research and scientific papers

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.

A six-step synthetic approach to marine natural product (+)-aureol

A concise synthetic approach to the marine natural product (+)-aureol has been achieved from readily available starting materials using obviously fewer steps in comparison to the related report in literature (6 steps versus 12 steps from (+)-sclareolide). Key steps of this protocol include a boron trifluoride-catalyzed domino 1,2-H and 1,2-methyl shifts and a nickel(II)-catalyzed cross-coupling reaction between an alkyl iodide and an aryl Grignard reagent.

Synthesis of Cyclosiphonodictyol A and Its Bis(sulfato)

The first synthesis of the marine benzoxepane hydroquinone cyclosiphonodictyol A and its bis(sulfato) from commercial (+)-sclareolide is reported. The key steps of the synthetic sequence (11 steps, 46% global) are the nucleophilic attack of a hindered tertiary alkoxide, a ring-closing metathesis reaction, and the Diels-Alder cycloaddition of a dienol acetate.

Regioselective 1,2-Diol Rearrangement by Controlling the Loading of BF3·Et2O and Its Application to the Synthesis of Related Nor-Sesquiterene- and Sesquiterene-Type Marine Natural Products

The regiocontrolled rearrangement of 1,2-diols has been achieved by controlling the loading of BF3·Et2O. Its applicability is showcased by the divergent synthesis of austrodoral, austrodoric acid, and 8-epi-11-nordriman-9-one, as well as a formal synthesis of siphonodictyal B and liphagal. A new light is shed on piancol-type rearrangements that will be useful in diversity-oriented synthesis of related natural products.

Synthesis of pelorol and its analogs and their inhibitory effects on phosphatidylinositol 3-kinase

There are numerous biologically active substances with novel structures and unique physiological functions in marine organisms. These substances are important sources of new lead compounds. Pelorol is a natural product isolated from marine organisms that possesses a novel structure with high bioactivity. In this paper, the synthesis of pelorol has been completed, and the synthesis of some intermediates has been optimized and scaled up. Five pelorol analogs have also been prepared. Preliminary biological activity testing demonstrated that compounds 5 and 6 might be potential lead compounds for cancer therapy.

A new strategy for efficient synthesis of medium and large ring lactones without high dilution or slow addition

We have developed an efficient method for medium and large ring lactone synthesis by a conceptually different ring-expansion strategy. The design of an unprecedented ring conjunction mode of oxetene, combined with the appropriate choice of a Lewis acid promoter and an additive, constitutes the key components of the new process. Enabled by this new approach, the reaction does not require high dilution or slow addition.

Scalable, divergent synthesis of meroterpenoids via "borono- sclareolide"

A scalable, divergent synthesis of bioactive meroterpenoids has been developed. A key component of this work is the invention of "borono- sclareolide", a terpenyl radical precursor that enables gram-scale preparation of (+)-chromazonarol. Subsequent synthetic operations on this key intermediate permit rapid access to a variety of related meroterpenoids, many of which possess important biological activity.

About a practical synthesis of Ambrox from sclareol: A new preparation of a ketone key intermediate and a close look at its Baeyer-Villiger oxidation

The latest route to Ambrox (1) starting from sclareol (2) proceeds through an oxy ketone 4 (Scheme 1). A new practical synthesis of the key intermediate 4 is described; it is equivalent to a partial oxidative degradation of sclareol (2) with peracetic and periodic acids (Scheme 2). The final product of the Baeyer - Villiger oxidation of the oxy ketone 4 with commercial peracetic acid is decisively dependent on the reaction conditions because the expected acetate 9 reacts with any nucleophile, especially the peracid (Scheme 3). Furthermore, this acetate 9 is very prone to eliminative coupling (Scheme 4).

An approach to furolabdanes and their photooxidation derivatives from R-(+)-sclareolide

A synthetic route to furolabdanes from commercially available R-(+)-sclareolide is reported, with the specific aim of preparing (12R and 12S,15ξ)-12,15-dihydroxylabda-7,13-dien-16,15-olides (3 and 5) and (12R and 12S, 16ξ)-12,16-dihydroxylabda-7,13-dien-15,16-olides (4 and 6). The key points of our approach are the use of Weinreb's amide 11 to join the furan ring to the terpenic unit. Photooxidation of the furan moiety of compounds 15 and 16, and of their acetates 19 and 20, has been used to built the hydroxybutenolide fragment. In this way the four possible isomers at the butenolide moiety, compounds 3-6, and their C-12 acetyl derivatives 21-24 have been obtained. On the basis of comparison of the spectral data (1H NMR) of the synthetic peracetates 25-28 (derived from 21-24) with the reported data for the peracetate 2 (derived from the natural product 1), the relative configuration at carbon C-12 of the natural product has been corrected. Furthermore, the absolute configuration of the natural product 1, considered to belong to the enantio-series, has to be changed to the normal-series on the basis of the optical rotation obtained for the synthetic derivative.

Ambergris compounds from labdanolic acid

Labdanolic acid (Cistus ladaniferus) is transformed into derivatives with amber odor. The strategy used allowed a process in which the oxidative decarboxylation reaction was carried out with the hydroxyl group protected.