1-Heptyne → a-[(tetrahydro-2H-pyran-2-yl)oxy]dec-4-yn-2(R)-ol

HRID 1195245

Reaction equation

HRID 1195245 reaction equation
CCCCC/C=C\C[C@@H](O)/C=[CH:11]/[CH:12]=[CH:13]/[CH:14]=[CH:15]\[C@@H:16](O)[CH2:17][CH2:18][CH2:19][C:20]([OH:22])=O.C1[O:27][C@H]1CO.O=C1O[C@H:36]([C@H:38]([CH2:40][OH:41])O)[C:34](O)=[C:32]1O.C#CCCCCC>CCOCC>[O:41]1[CH2:32][CH2:34][CH2:36][CH2:38][CH:40]1[O:22][CH2:20][C@H:19]([OH:27])[CH2:18][C:17]#[C:16][CH2:15][CH2:14][CH2:13][CH2:12][CH3:11]

Participants

6

Reactant 4

HCID 123501-HeptyneHCID 5280492Leukotriene B4HCID 6973630(-)-GlycidolHCID 54670067L-Ascorbic Acid

Product 1

HCID 14464847a-[(tetrahydro-2H-pyran-2-yl)oxy]dec-4-yn-2(R)-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

The starting material for the process of this invention, compound 2, can be prepared as described in Nicolaou, K. C. et al., "A General and Stereocontrolled Total Synthesis of Leukotriene B4 and Analogues," J. Am. Chem. Soc., 106, 3548 (1984) or Hanson, R. M. and Sharpless, K. B., J. Org. Chem., 51 1922 (1986). Briefly, optically active (S)-glycidol THP ether is prepared from ascorbic acid as disclosed in Takano, S., Numata, H., Ogasawara, K., Heterocycles, 19, 237 (1982) and Baldwin, J. J., Raab, A. W., Mensler, K., Arison, B. H., McClure, D. E., J. Org. Chem., 43, 4876 (1978). The ether is reacted (-78-25° C.) with two equivalents of the anion of 1-heptyne (1.0 equiv. of n-BuLi, 1.0 equiv. of TMEDA and THF, -78° C.) to afford a-[(tetrahydro-2H-pyran-2-yl)oxy] dec-4-yn-2(R)-ol which is then silylated (t-BuPh2SiCl, imidazole, DMF) to , compound 2.

Sources & evidence

ORD record
ord-b3da12420bdf42c095ff8497ef59c07f
Source dataset
uspto-grants-1992_05
Patent number
US05110949

Linked notes

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