Eur. J. Org. Chem. 2008 · © WILEY-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2008 · ISSN 1434–193X

SUPPORTING INFORMATION

Title: First Total Synthesis of the Potent Anticancer Natural Product Dideoxypetrosynol A: Preparation of the “Skipped” (Z)-Enediyne Moiety by Oxidative Coupling of Homopropargylphosphonium Ylide Author(s): Benjamin W. Gung,* Ann O. Omollo Ref. No.: O200800593

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324.2229

385.7547

363.7192349.1868

381.2791

431.1747429.2323

408.2522390.7692471.1149

454.5420437.1983

478.3286

478.5200

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84

18

Hz/c

n

t..

17

13824 DiacetateDd

m/z470 480 490 500 510 520 530 540 550 560 570 580 590 600

%

0

100Q051308M 101 (1.905) AM (Cen,4, 80.00, Ht,5000.0,0.00,1.00); Sm (SG, 2x3.00); Cm (101:112) TOF MS ES+

9.82e3472.6725

539.3115

513.2988

487.2895

481.2703

488.2946

498.2867

514.3083

523.2910

525.3006

540.3220

565.3351

541.3315

545.2971

566.3395

571.3107

597.2101572.3152

591.3505

Calculated M+Na 539.3137Measured M+Na 539.31154.1ppm

Internal Standard

18

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pm

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1 12

1 .6

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Hz

lcm

10

0

20

13824 monoacetateDd

m/z480 490 500 510 520 530 540 550 560 570 580 590 600 610 620 630

%

0

100Q051308J 201 (3.781) AM (Cen,4, 80.00, Ht,5000.0,0.00,1.00); Sm (SG, 2x3.00); Cm (191:201) TOF MS ES+

8.29e3497.3025

495.2939

481.2770

622.5667

498.3139

523.3262

503.2873

521.3114

529.3004

621.1866530.3049

597.1684553.4645

543.3235 555.3152 595.1717556.3190 613.1865 623.1915

Calculated M+Na 497.3032Measured M+Na 497.30251.4ppm

Internal Standard

21