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Mechanistic and computational studies of exocyclic stereocontrol in the synthesis of bryostatin-like cis-2,6-disubstituted 4-alkylidenetetrahydropyrans by Prins cyclization


, : Mechanistic and computational studies of exocyclic stereocontrol in the synthesis of bryostatin-like cis-2,6-disubstituted 4-alkylidenetetrahydropyrans by Prins cyclization. Journal of Organic Chemistry 78(1): 104-115

The Prins cyclization of syn-β-hydroxy allylsilanes and aldehydes gives cis-2,6-disubstituted 4-alkylidenetetrahydropyrans as sole products in excellent yields regardless of the aldehyde (R″) or syn-β-hydroxy allylsilane substituent (R') used. By reversing the R″ and R' groups, complementary exocyclic stereocontrol can be achieved. When the anti-β-hydroxy allylsilanes are used, the Prins cyclization gives predominantly cis-2,6-disubstituted 4-alkylidenetetrahydropyrans, now with the opposite olefin geometry in excellent yield. The proposed reaction mechanism and the observed stereoselectivity for these processes are supported by DFT calculations.

US$19.90

PMID: 23121542

DOI: 10.1021/jo301953h


Other references

Simon, K., 1959: The hazard of exaggerated fear of radiation in prevention of tuberculosis. Munchener Medizinische Wochenschrift 101: 2317-2318

Schmidt, H.; Vetter, A., 1982: Preliminary results on the effect of different soil moisture levels on yield and dry matter content of potatoes of maturity group 4 on a Lo2 site. In field trials in 1980-1, potatoes cv. Libelle were irrigated to give 40 or 60% utilizable field capacity from bud formation to the end of flowering and 40, 60 or 80% from the end of flowering to 70% abscission and were given 150 or 300 kg N + 24...

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Schwarz, F., 1951: Determination of visual acuity and intensity with different colored glasses. Pflugers Archiv 254(2): 144-154

Bocko, J., 1965: Displacement of iron in soil irrigated with sewage. Decomposition of sewage in soil causes oxygen deficit, resulting in a reduction of Fe3 and leaching of Fe2 to the lower horizons; the displaced Fe accumulates in the lower horizons, forming an impermeable layer inhibiting water percolation into th...

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DeWeese, J.A.; Adams, J.T.; Gaiser, D.L., 1970: Subclavian venous thrombectomy. Circulation 41(5 Suppl): Ii158-Ii164

Schaefer, C.W., 1964: Guide to Latin American scientific and technical periodicals An annotated list. Bulletin of the Entomological Society of America 10(2): 114-115

Bunyaratavej, N., 2012: The bone turnover markers in healthy Thai adults as the standard values. The present study of the bone markers in the healthy Thai females and males enrolled 588 females and 53 males with age range from 25 to 42 years. The potential modification of variations was controlled. The bone resorptive markers, betaCTx, of fem...

John, T.Jacob., 2008: Tuberculosis control: detect and treat infection in children. Indian Pediatrics 45(4): 261-264