2-Trans,6-trans,10-trans-geranylgeranyl diphosphate(3-) → Stemod-13(17)-ene

HRID 1172036Notes

Reaction equation

HRID 1172036 reaction equation
O([CH2:10]/[CH:11]=[C:12](/[CH2:14][CH2:15]/[CH:16]=[C:17](\[CH3:29])/[CH2:18][CH2:19]/[CH:20]=[C:21](/[CH2:23][CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])\[CH3:22])\[CH3:13])P(OP([O-])([O-])=O)(=O)[O-].CC1[C@H]2C[C@]3(CC2)[C@@H](CC[C@H]2C(C)(C)CCC[C@@]23C)C=1>CCCCC>[CH3:22][C@@:21]12[C@:16]34[CH2:15][C@H:14]([CH2:29][C@@H:17]3[CH2:18][CH2:19][C@H:20]1[C:26]([CH3:28])([CH3:27])[CH2:25][CH2:24][CH2:23]2)[C:12](=[CH2:13])[CH2:11][CH2:10]4

Participants

4

Reactant 2

HCID 54971052-Trans,6-trans,10-trans-geranylgeranyl diphosphate(3-)HCID 15161496Stemar-13-ene

Product 1

HCID 24798689Stemod-13(17)-eneYield 85%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

Chemicals. The preparations of (E,E,E)-geranylgeranyl diphosphate (GGPP), and ent- and syn-copalyl diphosphate (CPP), and syn-stemarene have been previously described. (Mohan et al. 1996). Stemodene standards were derived from a 1.5:1 mixture (ca. 5 mg) of synthetic racemic exo- and endo-stemodenes, kindly provided by Jim White. (White et al. 1994). This was fractionated by flash chromatography on a silica gel column (1 cm×10 cm) using pentane and the later eluting fractions (enriched for the exo isomer) were pooled and concentrated under nitrogen to yield ˜2 mg exo-stemodene (˜85% purity by GC analysis). Unless otherwise noted, chemicals were purchased from Fisher Scientific (Loughborough, Leicestershire, UK) and molecular biology reagents from Invitrogen (Carlsbad, Calif., USA).

Workup

  1. customkindly provided by Jim White
  2. washthe later eluting fractions (
  3. concentrationconcentrated under nitrogen

Sources & evidence

ORD record
ord-8176d06d5b934868a41922c3b6d98eb9
Source dataset
uspto-grants-2010_11
Patent number
US07833748B1

Reaction notes

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