Synthesis and evaluation of A-Ring diastereomers of 1α,25-dihydroxy-22-oxavitamin D 3 (OCT) 1

Hatakeyama, Susumi; Okano, Toshio; Maeyama, Junji; Esumi, Tomoyuki; Hiyamizu, Hiroko; Iwabuchi, Yoshiharu; Nakagawa, Kimie; Ozono, Keiichi; Akira, Kawase; Kubodera, Noboru

doi:10.1016/s0968-0896(00)00259-5

Cited by 15 publications

(9 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…According to the procedure described above, allylation of 4-pentenal (2.56 g, 30. ((2R,5R)-5-Allyltetrahydrofuran-2-yl)methanol (22). To a stirred suspension of 21 (909 mg, 7.20 mmol), Co(modp) 2 (776 mg, 1.44 mmol), and MS4A (0.92 g) in 2-propanol (67 mL) was added a 5.0−6.0 M solution of tert-butyl hydroperoxide in decane (1.50 mL), and the mixture was stirred at 50−52 °C for 6 h under an oxygen atmosphere, cooled to rt, and filtered through a pad of Celite.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Total Synthesis of the Proposed Structure for Aromin and Its Structural Revision

et al. 2016

View full text Add to dashboard Cite

This paper describes the first total synthesis of the proposed structure for aromin, an annonaceous acetogenin possessing an unusual bis-THF ring system, and its 4S,7R-isomer. The key steps involve an oxidative cyclization of a couple of terminal-diene alcohols and an intermolecular metathesis of an alkenyl tetrahydrofuran with an enone carrying a tetrahydrofuranyl lactone. The spectral data of both samples did not match those of aromin. Re-examination of the NMR data using the CAST/CNMR Structure Elucidator and chemical derivations suggested that the real structure of aromin should be revised to be a tetrahydropyran acetogenin, montanacin D. Cytotoxicities in human solid tumor cell lines for synthetic samples were also evaluated.

show abstract

Section: ■ Experimental Sectionmentioning

confidence: 99%

Total Synthesis of the Proposed Structure for Aromin and Its Structural Revision

et al. 2016

View full text Add to dashboard Cite

show abstract

“…169 There have been many reports of syntheses of vitamin D analogues with modifications to ring A and to the side chain. [170][171][172][173] These have included conformationally restricted mimics of vitamin D rotamers, 174,175 and some 21,24-methano derivatives. 176 [26, C]-1α,25-Dihydroxyvitamin D 3 has been synthesized 177 for use in positron emission tomography.…”

Section: Cholestanesmentioning

confidence: 99%

Steroids: reactions and partial synthesis

Hanson

2003

Nat. Prod. Rep.

View full text Add to dashboard Cite

show abstract

“…Unfortunately, however, the known preparations of 1 are long and tedious, discouraging the practical application of this useful approach. Thus, while many ingenious syntheses of 1 have been reported, only very recently has a synthesis of less than 10 steps been realized …”

Section: Introductionmentioning

confidence: 99%

Efficient Synthesis of the A-Ring Phosphine Oxide Building Block Useful for 1α,25-Dihydroxy Vitamin D₃and Analogues

et al. 2002

View full text Add to dashboard Cite

The 1 alpha-hydroxy A-ring phosphine oxide 1, a useful building block for vitamin D analogues, was synthesized from (S)-carvone in nine synthetic operations and a single chromatographic purification in 25% overall yield. The synthesis features two novel efficient synthetic transformations: the Criegee rearrangement of alpha-methoxy hydroperoxyacetate 10 in methanol to obtain directly the desired secondary 3 beta-alcohol 11 and the highly chemo- and stereoselective isomerization of dieneoxide ester (E)-7 to the 1 alpha-allylic alcohol with an exocyclic double bond (E)-8. Further insight into the selectivity control of the latter rearrangement was obtained from the reactions of (Z)-epimeric substrates. The new synthetic approach leading to the 1 alpha-hydroxy epimers complements our previously reported synthesis of the corresponding 1 beta-epimers, thus producing all stereoisomers of these versatile building blocks efficiently from carvone.

show abstract

Synthesis and evaluation of A-Ring diastereomers of 1α,25-dihydroxy-22-oxavitamin D 3 (OCT) 1

Cited by 15 publications

References 19 publications

Total Synthesis of the Proposed Structure for Aromin and Its Structural Revision

Total Synthesis of the Proposed Structure for Aromin and Its Structural Revision

Steroids: reactions and partial synthesis

Efficient Synthesis of the A-Ring Phosphine Oxide Building Block Useful for 1α,25-Dihydroxy Vitamin D₃and Analogues

Contact Info

Product

Resources

About

Synthesis and evaluation of A-Ring diastereomers of 1α,25-dihydroxy-22-oxavitamin D 3 (OCT) 1

Cited by 15 publications

References 19 publications

Total Synthesis of the Proposed Structure for Aromin and Its Structural Revision

Total Synthesis of the Proposed Structure for Aromin and Its Structural Revision

Steroids: reactions and partial synthesis

Efficient Synthesis of the A-Ring Phosphine Oxide Building Block Useful for 1α,25-Dihydroxy Vitamin D3and Analogues

Contact Info

Product

Resources

About

Efficient Synthesis of the A-Ring Phosphine Oxide Building Block Useful for 1α,25-Dihydroxy Vitamin D₃and Analogues