8α,13β-epoxy-15-norlabdan-14-oic acid

Base Information

• Chemical Name: 8α,13β-epoxy-15-norlabdan-14-oic acid
• CAS No.: 52154-07-1
• Molecular Formula: C₁₉H₃₂O₃
• Molecular Weight: 308.461
• Mol file: 52154-07-1.mol

Synonyms:

Chemical Property of 8α,13β-epoxy-15-norlabdan-14-oic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8α,13β-epoxy-15-norlabdan-14-oic acid

There total 1 articles about 8α,13β-epoxy-15-norlabdan-14-oic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 59.0%

manoyl oxide (596-84-9) → sclareol oxide (5153-92-4) + 8α,13β-epoxy-15-norlabdan-14-oic acid (52154-07-1) + 8α,13β-epoxy-15-hydroxylabdan-12-one (117015-27-7)

Guidance literature:

With potassium permanganate; acetic acid; In water; acetone; for 0.5h;

Reference yield: 3.0%

8α,13β-epoxy-15-norlabdan-14-oic acid (52154-07-1) + lead(IV) tetraacetate (546-67-8) → sclareol oxide (5153-92-4) + 8α,13-epoxy-14,15-bisnorlabd-12-en-12-yl acetate (130451-61-5) + 8α,13-epoxy-14,15-bisnorlabd-12-en-16-yl acetate (130451-62-6)

Guidance literature:

With pyridine; copper diacetate; In tetrahydrofuran; at 60 ℃; for 0.5h;

Reference yield:

8α,13β-epoxy-15-norlabdan-14-oic acid (52154-07-1) → (-)-pumiloxide (67779-53-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 78 percent / pyridine, copper(II) acetate / tetrahydrofuran / 0.5 h / 60 °C

2: 71 percent / Jones reagent / acetone / 1.) -40 deg C, 45 min, 2.) 0 deg C, 30 min

4: 85 percent / red-Al / toluene / 0.5 h / Ambient temperature

5: 1.) p-toluenesulfonyl chloride, s-collidine, 2.) LiCl / 1.) CH₂Cl₂, RT, 2 h, 2.) DMF, 2 h

6: 65 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / Ambient temperature

With pyridine; 2,4,6-trimethyl-pyridine; lithium aluminium tetrahydride; jones reagent; copper diacetate; p-toluenesulfonyl chloride; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium chloride; In tetrahydrofuran; acetone; toluene;

upstream raw materials:

manoyl oxide

Downstream raw materials:

sclareol oxide

8α,13-epoxy-14,15-bisnorlabd-12-en-12-yl acetate

8α,13-epoxy-14,15-bisnorlabd-12-en-16-yl acetate

(-)-pumiloxide