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Tetrahedron Letters
Volume 27, Issue 2, 1986, Pages 231-234

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doi:10.1016/S0040-4039(00)83984-2

Synthesis of chiral 1,2-diols and related compounds of biological activities via stepwise ring fission of 5-alkyl-6,8-dioxabicyclo[3.2.1]octane skeleton

Yukio Masaki, ^*, Yuzuru Serizawa, Kinnosuke Nagata, Hirohisa Oda, Hiromu Nagashima and Kenji Kaji

Gifu Pharmaceutical University, 5-6-1 Mitahora Higashi, Gifu 502, Japan

Received 14 November 1985.

Available online 8 March 2001.

Abstract

5-Alkyl-7-mesyloxymethyl-6,8-dioxabicyclo[3.2.1]octanes , prepared from (+)-tartaric acid, were converted by means of an organoaluminium reagent Et₂AlSPh into the pyranoid monothioacetals, which were utilized via the successive thioacetalization to the synthesis of the insect pheromones (+)-disparlure and (−)-(2S,3S)-octanediol.

References

D. Seebach and E. Hungerb hler In: R. Scheffold, Editor, Modern Synthetic Methods 2, Otto Salle Verlag, Frankfurt am Main (1980), p. 91.
K. Mori In: J. ApSimon, Editor, The Total Synthesis of Natural Products 4, Wiley, New York (1981), p. 1. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (5)

Y. Masaki, K. Nagata, Y. Serizawa and K. Kaji Tetrahedron Lett. 23 (1982), p. 5553. Abstract | PDF (143 K) | View Record in Scopus | Cited By in Scopus (5)
Y. Masaki, K. Nagata, Y. Serizawa and K. Kaji Tetrahedron Lett. 25 (1984), p. 95. Abstract | PDF (140 K) | View Record in Scopus | Cited By in Scopus (7)
Y. Masaki, Y. Serizawa, K. Nagata and K. Kaji Chem. Lett. (1983), p. 1601. Full Text via CrossRef
Y. Masaki, K. Nagata and K. Kaji Chem. Lett. (1983), p. 1835. Full Text via CrossRef

M. Cerny and J. Stanek, Jr. In: R.S. Tipson and D. Horton, Editors, Advance in Carbohydrate Chemistry and Biochemistry 34, Academic Press, New York (1977), p. 23. Abstract

Y. Kim and B.P. Mundy J. Org. Chem. 47 (1982), p. 3556. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (13)

Y. Masaki, Y. Serizawa, K. Nagata and K. Kaji Chem. Lett. (1984), p. 2105. Full Text via CrossRef

K. Oshima and H. Nozaki J. Synth. Org. Chem. Jpn. 38 (1980), p. 460.
K. Maruoka and H. Yamamoto J. Synth. Org. Chem. Jpn. 43 (1985), p. 429. View Record in Scopus | Cited By in Scopus (0)

T. Sakai, Y. Nakagawa, J. Takahashi, K. Iwabuchi and K. Ishii Chem. Lett. (1984), p. 263. Full Text via CrossRef

E. Abushanab, M. Bessodes and K. Antonakis Tetrahedron Lett. 25 (1984), p. 3841. Abstract | PDF (182 K) | View Record in Scopus | Cited By in Scopus (14)
G. Bastian, M. Bessodes, R.P. Panzica, E. Abushanab, S-F. Chen, J.D. Stoeckler and R.E. Parks, Jr. J. Med. Chem. 24 (1981), p. 1383. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (5)

B.A. Bierl, M. Beroza and C.W. Collier Science 170 (1970), p. 87. View Record in Scopus | Cited By in Scopus (47)
K. Mori, T. Takigawa and M. Matsui Tetrahedron 35 (1979), p. 833. Abstract | PDF (571 K) | View Record in Scopus | Cited By in Scopus (9)

The pheromone (12) and the azide (14) synthesized were identified respectively with the corresponding authentic samples 12 ([α]_D−19.2° (c=1.45, CHCl₃))⁷⁾ and 14 ([α]_D+13.4° (c=1.31))⁸⁾ by spectral comparison.

H. Loibner and E. Zbiral Helv. Chim. Acta. 59 (1976), p. 2100. Full Text via CrossRef

Tetrahedron Letters
Volume 27, Issue 2, 1986, Pages 231-234

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