Production Method 1

37428-56-1

86365-83-5

Reaction Conditions

1.1 Reagents: Phosphorus tribromide Solvents: Diethyl ether ;  rt → 0 °C; 5 min, 0 °C; 15 min, 0 °C

Reference

Constructing the architecturally distinctive ABD-tricycle of phomactin A through an intramolecular oxa-[3+3] annulation strategy

Buchanan, Grant S.; et al, Tetrahedron, 2011, 67(52), 10105-10118

Production Method 2

37428-56-1

86365-83-5

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Dichloromethane
2.1 Reagents: Lithium bromide Solvents: Tetrahydrofuran

Reference

Vinyl radical cyclization in the synthesis of natural products: seychellene

Stork, Gilbert; et al, Tetrahedron Letters, 1985, 26(48), 5927-30

Production Method 3

4021-75-4

86365-83-5

Reaction Conditions

1.1 Reagents: Lithium diisopropylamide
1.2 Solvents: Tetrahydrofuran ;  < -70 °C; 90 min, < -70 °C; 2 h, < -70 °C
1.3 Reagents: Methanol ;  < -70 °C; < -70 °C → rt
1.4 Reagents: Hydrochloric acid Solvents: Water ;  acidified, rt
2.1 Reagents: Phosphorus tribromide Solvents: Diethyl ether ;  rt → 0 °C; 5 min, 0 °C; 15 min, 0 °C

Reference

Constructing the architecturally distinctive ABD-tricycle of phomactin A through an intramolecular oxa-[3+3] annulation strategy

Buchanan, Grant S.; et al, Tetrahedron, 2011, 67(52), 10105-10118

Production Method 4

54899-03-5

86365-83-5

Reaction Conditions

1.1 Reagents: Hexamethylphosphoramide ,  Lithium diisopropylamide Solvents: Tetrahydrofuran ;  0 °C; 90 min, < -70 °C; 2 h
2.1 Reagents: Phosphorus tribromide Solvents: Diethyl ether ;  rt → 0 °C; 5 min, 0 °C; 15 min, 0 °C

Reference

An enantioselective synthesis of the ABD tricycle for (-)-phomactin A featuring Rawal's asymmetric Diels-Alder cycloaddition

You, Ling-Feng; et al, Advanced Synthesis & Catalysis, 2008, 350(18), 2885-2891

Production Method 5

504-61-0

86365-83-5

Reaction Conditions

1.1 Reagents: Bromine Solvents: Dichloromethane ;  rt → -40 °C; -40 - -30 °C; -30 °C → rt
2.1 Reagents: Lithium diisopropylamide
2.2 Solvents: Tetrahydrofuran ;  < -70 °C; 90 min, < -70 °C; 2 h, < -70 °C
2.3 Reagents: Methanol ;  < -70 °C; < -70 °C → rt
2.4 Reagents: Hydrochloric acid Solvents: Water ;  acidified, rt
3.1 Reagents: Phosphorus tribromide Solvents: Diethyl ether ;  rt → 0 °C; 5 min, 0 °C; 15 min, 0 °C

Reference

Constructing the architecturally distinctive ABD-tricycle of phomactin A through an intramolecular oxa-[3+3] annulation strategy

Buchanan, Grant S.; et al, Tetrahedron, 2011, 67(52), 10105-10118

Production Method 6

69169-56-8

86365-83-5

Reaction Conditions

1.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran
2.1 Reagents: Triethylamine Solvents: Dichloromethane
3.1 Reagents: Lithium bromide Solvents: Tetrahydrofuran

Reference

Vinyl radical cyclization in the synthesis of natural products: seychellene

Stork, Gilbert; et al, Tetrahedron Letters, 1985, 26(48), 5927-30

Production Method 7

37428-56-1

86365-83-5

Reaction Conditions

1.1 Reagents: Phosphorus tribromide Solvents: Diethyl ether ;  rt → 0 °C; 5 min, 0 °C; 15 min, 0 °C

Reference

An enantioselective synthesis of the ABD tricycle for (-)-phomactin A featuring Rawal's asymmetric Diels-Alder cycloaddition

You, Ling-Feng; et al, Advanced Synthesis & Catalysis, 2008, 350(18), 2885-2891

Production Method 8

37428-56-1

86365-83-5

Reaction Conditions

Reference

Studies toward brevisulcenal F via convergent strategies for marine ladder polyether synthesis

Katcher, Matthew H.; et al, Tetrahedron, 2018, 74(11), 1111-1122

Production Method 9

105479-82-1

86365-83-5

Reaction Conditions

1.1 Reagents: Lithium bromide Solvents: Tetrahydrofuran

Reference

Vinyl radical cyclization in the synthesis of natural products: seychellene

Stork, Gilbert; et al, Tetrahedron Letters, 1985, 26(48), 5927-30

Production Method 10

22122-36-7

86365-83-5

Reaction Conditions

Reference

Studies toward brevisulcenal F via convergent strategies for marine ladder polyether synthesis

Katcher, Matthew H.; et al, Tetrahedron, 2018, 74(11), 1111-1122

Production Method 11

86365-83-5

Reaction Conditions

1.1 Reagents: Bromine Solvents: Dichloromethane ;  rt → -40 °C; -40 - -30 °C; -40 °C → rt
2.1 Reagents: Hexamethylphosphoramide ,  Lithium diisopropylamide Solvents: Tetrahydrofuran ;  0 °C; 90 min, < -70 °C; 2 h
3.1 Reagents: Phosphorus tribromide Solvents: Diethyl ether ;  rt → 0 °C; 5 min, 0 °C; 15 min, 0 °C

Reference

An enantioselective synthesis of the ABD tricycle for (-)-phomactin A featuring Rawal's asymmetric Diels-Alder cycloaddition

You, Ling-Feng; et al, Advanced Synthesis & Catalysis, 2008, 350(18), 2885-2891

Production Method 12

689-97-4

86365-83-5

18668-68-3

Reaction Conditions

Reference

Synthesis of linear allenes by addition

Wang, K. K., Science of Synthesis, 2007, 44, 229-286

2-Butene, 1,3-dibromo-, (2E)- (9CI, ACI) Raw materials

• 3-Methyl-2(5H)-furanone
• (2E)-but-2-en-1-ol
• (E)-3-bromobut-2-en-1-ol
• 1-BUTANOL, 2,3-DIBROMO-, (R*,S*)-
• 2,3-dibromobutan-1-ol
• 3-bromobut-2-en-1-ol;methanesulfonic Acid
• 2-Butenoic acid, 3-bromo-, (2E)-
• 1-BUTEN-3-YNE

2-Butene, 1,3-dibromo-, (2E)- (9CI, ACI) Preparation Products

• 4-Bromobuta-1,2-diene (18668-68-3)
• 2-Butene, 1,3-dibromo-, (2E)- (9CI, ACI) (86365-83-5)

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