541501-07-9

Upstream product

• 541501-04-6 [3R,4aS,6R,8aS]-3-benzyloxy-8-iodo-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalene 
• 541501-02-4 (4aS,6R,8aS)-6-Benzyloxy-2,5,5,8a-tetramethyl-octahydro-naphthalen-1-one 
• 614719-20-9 [2R,4aS,6R,8aS]-6-benzyloxy-2,5,5,8a-tetramethyloctahydronaphthalen-1-ylidenehydrazine 
• 541501-06-8 3,5-Bis-benzyloxy-4-[((4aR,6R,8aS)-6-benzyloxy-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-hydroxy-methyl]-benzoic acid tert-butyl ester 

Downstream Products

• 541501-08-0 3,5-Bis-benzyloxy-4-((4aR,6R,8aS)-6-benzyloxy-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-benzoic acid methyl ester 
• 541501-10-4 3,5-Dihydroxy-4-((4aR,6R,8aS)-6-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-benzoic acid methyl ester 
• 163391-76-2 stachybotrylactam 
• 541501-09-1 [2R,4aS,6R,8aS]-4-(6-benzyloxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-ylmethyl)-3,5-dihydroxybenzoic acid methyl ester 
• 541501-14-8 [1'⁽²⁾R,2'R,4'aS,6'R,8'aS]-4-benzyloxy-5-bromo-6'-hydroxy-3',4',4'a,5',6',7',8',8'a-octahydro-2',5',5',8'a-tetramethylspiro[benzofuran-2(3H),1'(2'H)-naphthalene]-6-carboxylic acid methyl ester 
• 541501-17-1 [1'⁽²⁾R,2'R,4'aS,6'R,8'aS]-4-benzyloxy-7-bromo-6'-hydroxy-3',4',4'a,5',6',7',8',8'a-octahydro-2',5',5',8'a-tetramethylspiro[benzofuran-2(3H),1'(2'H)-naphthalene]-6-carboxylic acid methyl ester 
• 541501-15-9 [1'⁽²⁾R,2'R,4'aS,6'R,8'aS]-4-benzyloxy-5-cyano-6'-hydroxy-3',4',4'a,5',6',7',8',8'a-octahydro-2',5',5',8'a-tetramethyspiro[benzofuran-2(3H),1'(2'H)-naphthalene]-6-carboxylic acid methyl ester 
• 541501-18-2 [1'⁽²⁾R,2'R,4'aS,6'R,8'aS]-6'-hydroxy-7-cyano-3',4',4'a,5',6',7',8',8'a-octahydro-2',5',5',8'a-tetramethylspiro[benzofuran-2(3H),1'(2'H)-naphthalene]-6-carboxylic acid methyl ester 
• 541501-16-0 [1'⁽²⁾R,2'R,4'aS,6'R,8'aS]-4-(tert-butyldiphenylsilyloxy)-6'-hydroxy-3',4',4'a,5',6',7',8',8'a-octahydro-2',5',5',8'a-tetramethylspiro[benzofuran-2(3H),1'(2'H)-naphthalene]-6-carboxylic acid methyl ester 
• 614719-22-1 [1'⁽²⁾R,2'R,4'aS,6'R,8'aS]-4-benzyloxy-7-formyl-6'-hydroxy-3',4',4'a,5',6',7',8',8'a-octahydro-2',5',5',8'a-tetramethylspiro[benzofuran-2(3H),1'(2'H)-naphthalene]-6-carboxylic acid methyl ester 
• 614719-21-0 [1'⁽²⁾R,2'R,4'aS,6'R,8'aS]-4-benzyloxy-7-ethenyl-6'-hydroxy-3',4',4'a,5',6',7',8',8'a-octahydro-2',5',5',8'a-tetramethylspiro[benzofuran-2(3H),1'(2'H)-naphthalene]-6-carboxylic acid methyl ester 
• 541501-19-3 C₃₉H₄₉BrO₅Si 

Relevant academic research and scientific papers

Enantioselective total synthesis and structure revision of spirodihydrobenzofuranlactam 1. Total synthesis of stachybotrylactam

(Matrix presented) The enantioselective total synthesis and structure revision of spirodihydrobenzofuranlactam 1 and of its regioisomer 25 are presented. Optically pure (+)-Wieland-Miescher ketone was utilized to construct the AB bicyclic core in 10 steps

Total synthesis and structure revision of Stachybotrys spirolactams

The spirolactam structure 1 reported in 1996 by Roggo et al. has been enantioselectively synthesized in 20 steps from (+)-Wieland-Miescher ketone. Spectra of this synthetic lactam differed from those of the natural spirolactam from the Roggo group, leading to the hypothesis that the natural lactam may be the regioisomer 27, a structure previously ascribed by Jarvis et al. to the natural product stachybotrylactam. This hypothesis was confirmed by the first total synthesis of (-)-stachybotrylactam (27). Double reductive amination of two molecules of aldehyde 29 with one molecule of L-lysine led by analogous chemistry to the first synthesis of the pseudosymmetric "dimer" 30, whose spectra corresponded to those of the natural "dimer" originally assigned structure 5 by the Roggo group.