Process for the synthesis of alpha-methylene-gamma-butyrolactone

A process for the preparation of 4-acetoxy-2-methylene-butan-1-ol, said process comprising the steps of:

• a) acetylating the C1-hydroxyl group of isoprenol to yield isoprenyl acetate;
• b) forming 4-acetoxy-2-methylene-butan-1-ol from said isoprenyl acetate by whole cell biotransformation, said step comprising:
• i) contacting a cell (CB) with a culture medium containing said isoprenyl acetate or with a culture medium contiguous with an organic phase containing said isoprenyl acetate under conditions that enable the cell to form 4-acetoxy-2-methylene-butan-1-ol from isoprenyl acetate;
• and,
• ii) isolating the resultant 4-acetoxy-2-methylene-butan-1-ol,
• wherein said cell (CB) exhibits activity of at least one alkane monooxygenase enzyme which catalyzes the formation of 4-acetoxy-2-methylene-butan-1-ol from isoprenyl acetate.

A process for the preparation of 2-methylenebutan-1,2-diol, said process comprising the steps of:

• a) acetylating the C1-hydroxyl group of isoprenol to yield isoprenyl acetate;
• b) forming 4-acetoxy-2-methylene-butan-1-ol from said isoprenyl acetate by whole cell biotransformation, said step comprising:
• i) contacting a cell (CB) with a culture medium containing said isoprenyl acetate or with a culture medium contiguous with an organic phase containing said isoprenyl acetate under conditions that enable the cell to form 4-acetoxy-2-methylene-butan-1-ol from isoprenyl acetate;
• and,
• ii) isolating the resultant 4-acetoxy-2-methylene-butan-1-ol,
• wherein said cell (CB) exhibits activity of at least one alkane monooxygenase enzyme which catalyzes the formation of 4-acetoxy-2-methylene-butan-1-ol from isoprenyl acetate;
• and,
• c) hydrolysis of said 4-acetoxy-2-methylene-butan-1-ol to form 2-methylenebutan-1,2-diol.

A process for preparing a compound of Formula (BIII) from a compound of Formula (BII) by whole cell biotransformation:

• wherein:
• n is an integer of from 0 to 8;
• R1 is C1-C4 alkyl;
• R2 is H or C1-C4 alkyl;
• and,
• R3 is H or C1-C4 alkyl,
• said process comprising:
• i) contacting a cell (CB) with a culture medium containing said compound of Formula (BII) or with a culture medium contiguous with an organic phase containing said compound of Formula (BII) under conditions that enable the cell to form said compound of Formula (BIII) from said compound of Formula (BII);
• and,
• ii) isolating the resultant compound of Formula (BIII),
• wherein said cell (CB) exhibits activity of at least one alkane monooxygenase enzyme which catalyzes the Cn+3-hydroxylation of said compound of Formula (BII).