@article{47262adcfd6b4bd69573af027bffabce,
title = "Steroids and related natural products-X. Reduction of lactones",
abstract = "Boron trifluoride etherate-lithium aluminum hydride reduction of 12β-hydroxy-14ξ-rosane 16-carboxylic acid lactone (IIa), dihydroabietic γ-lactone (IIIa) and 3β-hydroxy-7-oxo-7a-oxa-B- homo-5α-cholestane (Xa) was found to yield the corresponding (IIb and IIIb) and oxepane (Xb, after acetylation) derivatives. Similar reduction of several lactones prepared from primary alcohols resulted in essentially complete conversion to their respective glycols. For example, only 3,4-dihydroxy-3,4-seco-5α-androstane (IX) was isolated following reduction of 3-oxo-3a-oxa-A-homo- 5α-androstane (VII). The present study suggests that boron trifluoride-lithium aluminum hydride reduction of esters will increasingly favor ether formation as branching adjacent to the ester alkyl-oxygen moiety increases.",
author = "Pettit, {G. R.} and B. Green and Kasturi, {T. R.} and Ghatak, {U. R.}",
note = "Funding Information: 1 Previous contribution: G. R. Pettit and B. Green, J. Org. Chem. 26, 4473 (1961). 2 This investigation was supported by PHS Research Grants CY_4074(C2) and CY_4074(C3) from the National Cancer Institute, Public Health Service; National Science Foundation Research Grants G-9585 and G-19500; and was aided by Grant T-79A from the American Cancer Society. a F. Beilstein, Handbuch der Orgmi.schen Chemie Vol. I; p. 293, Voss Verlag, Hamburg (1893). 4 Compare the work of Rose and Wittstock, Pqg. Ann. 48,463 (1840) [Chem. Zentr. I&2.( 1840)J; A. W. Williamson, J. Chem. Sot. 4, 229 (1851); A. W. Williamson, Liebigs Ann. 81, 77 (1852); S Marasse, Ibid 152, 59 (1869); L. M. Norton and C. 0. Prescott, Amer. Chem. J. 6,241 (1884); and the recent studies of R. H. Baker and W. B. Martin, J. Org. Chem. 25,1496 (1960); S. Searles, D. G. Hummel, S. Nukina and P. E. Throckmorton, J. Amer. Chem. Sac. 82, 2928 (1960); J. Kalvoda, G. Anner, D. Arigoni, K. Heusler, H. Immer, 0. Jeger, M. Lj. MihailoviC, K. SchafTner and A. Wettstein, Helo. Chim. Acfa 44,186 (1961); R. Lombard and G. Ambroise, Bull. Sot. chim. Fr. 230 (1961); P. Piganiol, J. Cheymol, J. Seyden-Penne and P. Chabrier, Ibid. 255 (1961); and J. S. Mills and V. Petrow, C&m. & Ind. 946 (1961). 5 C. Mettler, Ber. Dtsch. Chem. Ges. 37, 3692 (1904). d Cf. G. R. Pettit and T. R. Kasturi, J. Org. ChePn. 26,4553 (1961). Recently, J. N. Ray, A. Mukherji and N. D. Gupta, J. Ind. Chem. Sm. 38, 705 (1961), reported reduction of acetyl methyl salicylatc to oethoxy methyl benzoate using aluminum amalgam. 7 G. R. Pettit and T. R. Kasturi, J. Org. Chem. 25,875 (1964Q 8 G. R. Pettit, U. R. Ghatak, Brian Green, T. R. Kasturi and D. M. Piatak, J. Org. Chem. 26, 1685 (1961). @G . R. Pettit and T. R. Kasturi, J. Org. Chcm. 26,4557 (1961). 953",
year = "1962",
doi = "10.1016/S0040-4020(01)92749-8",
language = "English (US)",
volume = "18",
pages = "953--958",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "8",
}