pentanoate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a manner similar to that set forth in A, but substituting for acetic anhydride, the anhydrides or halides of propionic, butanoic, pentanoic, or hexanoic acid, the corresponding manoalide δ-lactone propionate, butanoate, pentanoate, and hexanoate are prepared.

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In another preparation of the aforesaid valerate, isobutyraldehyde (0.72 g) was added to a mixture of [(1-methoxy-2-methyl-1-propenyl)oxy]trimethylsilane (1.74 g, 10 mmol) and (TAS)HF2 (100 mg, 0.1 mmol) in 20 mL of tetrahydrofuran under argon at -11°. The reaction mixture was stirred and the temperature was allowed to rise to 23°. Stirring was continued for 18 h and the mixture was then poured into 200 mL of ethyl acetate and extracted with water (200 mL), followed by washing with aqueous brine (200 mL). The organic layer was dried (MgSO4), filtered and evaporated in vacuo to give 2.39 g (97% yield) of methyl 2,2,4-trimethyl-3-trimethylsiloxyvalerate. to rise to 23° Stirring extracted with water (200 mL) by washing with aqueous brine (200 mL) The organic layer was dried (MgSO4) filtered evaporated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In another preparation of the aforesaid valerate, isobutyraldehyde (0.72 g) was added to a mixture of [(1-methoxy-2-methyl-1-propenyl)oxy]trimethylsilane (1.74 g, 10 mmol) and (TAS)HF2 (100 mg, 0.1 mmol) in 20 mL of tetrahydrofuran under argon at -11°. The reaction mixture was stirred and the temperature was allowed to rise to 23°. Stirring was continued for 18 h and the mixture was then poured into 200 mL of ethyl acetate and extracted with water (200 mL), followed by washing with aqueous brine (200 mL). The organic layer was dried (MgSO4), filtered and evaporated in vacuo to give 2.39 g (97% yield) of methyl 2,2,4-trimethyl-3-trimethylsiloxyvalerate. to rise to 23° Stirring extracted with water (200 mL) by washing with aqueous brine (200 mL) The organic layer was dried (MgSO4) filtered evaporated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a manner similar to that set forth in A, but substituting for acetic anhydride, the anhydrides or halides of propionic, butanoic, pentanoic, or hexanoic acid, the corresponding manoalide δ-lactone propionate, butanoate, pentanoate, and hexanoate are prepared.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a manner similar to that set forth in Paragraph A, but substituting for acetic anhydride, the anyhydrides or halides of proprionic, butanoic, pentanoic, or hexanoic acid, the corresponding manoalide δ-lactone proprionate, butanoate, pentanoate, and hexanoate are prepared.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a manner similar to that set forth in Paragraph A, but substituting for acetic anhydride, the anyhydrides or halides of proprionic, butanoic, pentanoic, or hexanoic acid, the corresponding manoalide δ-lactone proprionate, butanoate, pentanoate, and hexanoate are prepared.